Klitschko was born in Semipalatinsk (now Semey), Kazakh SSR, Soviet Union (now Kazakhstan). His father, Vladimir Rodionovic Klitschko (1947–2011), was a Soviet Air Force major general and a military attaché of Ukraine in Germany; he was also one of the commanders in charge of cleaning up the effects of the Chernobyl disaster in 1986 and was afterward diagnosed with cancer. Wladimir’s mother is Nadezhda Ulyanovna. He is the younger brother of former WBC, WBO and Ring magazine heavyweight champion Vitali Klitschko, the current Mayor of Kyiv.

Klitschko started training in amateur boxing with Brovary Olympic Reserve School in the late 1980s. In the early 1990s, Klitschko was coached in Poland’s Gwardia Warszawa boxing club, where, according to Jerzy Kulej, “He and his brother used to demolish our boys.” In 1993, he won the Junior European Championships as a heavyweight. In 1994, he received 2nd place at the Junior World Championships in Istanbul, Turkey, losing to Cuban Michel López Núñez in the finals. In 1995, he won the gold medal at the Military Championships in Ariccia, Italy, defeating Luan Krasniqi, who he had lost to in the third round of the World Championships in Berlin, Germany earlier that year. In 1996, he captured 2nd place as a Super Heavyweight at the European Championships in Vejle, Denmark losing to Alexei Lezin in the finals. He defeated Lezin later that year in the semi finals at the 1996 Summer Olympics in Atlanta. He had an amateur record of 134–6.

Klitschko turned professional with Universum Box-Promotion in Hamburg under the tutelage of Fritz Sdunek, often being featured on fight cards alongside his elder brother Vitali. After building an undefeated record of 24–0 with 21 KOs, he suffered his first loss to 24–13–1 Ross Puritty, in what was Klitschko’s first and only professional fight in Ukraine. Puritty forced Klitschko, who had at that time not gone beyond eight rounds, to punch himself out. Klitschko began to be overwhelmed in the tenth round and went down twice but was allowed to continue. At the start of the eleventh round, with Puritty continuing to land hard punches, Klitschko’s trainer, Fritz Sdunek, entered the ring and stopped the fight. Three years later, Klitschko’s brother Vitali stopped Puritty in the eleventh round himself. On 18 March 2000, Klitschko fought Paea Wolfgramm, whom he fought previously in the 1996 super-heavyweight Olympic finals. In their professional rematch, Klitschko knocked Wolfgramm out in the first round.

Wladimir Klitschko got his chance to fight for the world heavyweight championship on 14 October 2000 against WBO champion Chris Byrd. Byrd, considered one of the most avoided fighters in the heavyweight division at the time, won the title six months earlier on 1 April from Wladimir’s brother Vitali (who had a perfect record of 27 fights, 27 wins, 27 KOs coming into the fight), being a late replacement for Donovan Ruddock. In that fight, Byrd was trailing on the scorecards (83–88, 83–88, & 82–89) but was declared the winner after Vitali retired on his stool between 9th and 10th rounds due to shoulder injury. Byrd’s title defence against Wladimir was scheduled to take place at Kölnarena in Cologne and was billed as “Revenge Of The Brother”. In a fight that was aired on pay-per-view in the United Kingdom, Wladimir won the WBO world heavyweight title from Byrd by a wide unanimous decision (UD) with scores of 120–106, 119–107, and 118–108, flooring his opponent twice.

Klitschko’s first defence of the WBO title came on 24 March 2001 against Derrick Jefferson. Jefferson, regarded as a big and athletic brawler and a fan-friendly attraction, was coming into the bout with a record of 23 wins in 26 bouts, with 19 of those wins coming inside the distance (18 of them inside the first three rounds, 11 of them – in the first round). Jefferson was mostly known for the sixth-round knockout (KO) of Maurice Harris, which was named The Ring Knockout of the Year in 1999. He was 4–2 in the last six fights, losing by technical knockout (TKO) to David Izon, in a fight he was winning on the scorecards but punched himself out, and Oleg Maskaev in round four after breaking an ankle during a first knockdown in the first round.

Klitschko’s next title defence was scheduled less than five months later on 4 August 2001. The fight took place at the Mandalay Bay Events Center in Paradise, Nevada against hometown fighter, Charles Shufford. At the time, Shufford had a 17–1 record, coming off of wins against Jimmy Thunder and Lamon Brewster. Shufford weighed in at 234 lbs., 17 pounds lighter than in his previous bout. Shufford, having played George Foreman opposite Will Smith in the movie Ali, entered the ring with Smith by his side. Klitschko knocked Shufford down three times, once in round two, once in round three (both times with a straight right hand) and in round six with a left hook, with referee stopping the bout after the third knockdown. According to punch stats, Klitschko landed 58 of 262 punches (22%) and Shufford connected on 16 of 190 (8%).

Klitschko had his next title defence scheduled three months later, on 29 June 2002 at Etess Arena in Atlantic City, New Jersey, against former WBO heavyweight champion Ray Mercer. It was the first time in his professional career that Klitschko fought an Olympic Gold medalist. 41-year old Mercer, having fought Lennox Lewis and Evander Holyfield throughout his career, was expected to be a tough challenge for Klitschko that would give him and Lennox Lewis, the WBC and The Ring champion, a second common opponent (along with Francois Botha) and a bout comparable to Lewis vs. Tyson. During the build-up to the bout, Mercer referred to Klitschko as “Russian Tommy Morrison”. Since his comeback in 2001, Mercer had won four fights over journeymen, three of them inside two rounds, prior to the Klitschko bout.

Klitschko returned to Mandalay Bay Event Center for his sixth defence on 7 December 2002 against Jameel McCline. McCline, having made his professional boxing debut in 1995, became an established contender after defeating Michael Grant, knocking him down with the first punch thrown and ultimately stopping him in 43 seconds. Prior to fighting Klitschko, McCline had defeated two more heavyweight contenders, Lance Whitaker and Shannon Briggs, by wide unanimous decisions. Being 6 ft 6 in tall with an 82 in reach, McCline was of similar height and longer reach than Klitschko, while also being 22 lbs heavier. Many opinion polls gave Klitschko a 60–40 advantage over McCline. The fight was the main event of the card that also featured Floyd Mayweather Jr. defending the WBC lightweight title against Jose Luis Castillo.

Klitschko suffered an upset TKO loss to Corrie Sanders on 8 March 2003 in Hanover, Germany. Sanders dropped Klitschko twice in the opening round and scored two more knockdowns in the second round before the bout was stopped by the official. The fight was named The Ring magazine Upset of the Year for 2003.

The Klitschkos were also considered big stars in Germany. According to DW, a research conducted no later than 2011 showed that nearly 99% of people in Germany recognized the Klitschko brothers; a similar research carried out by TNS for the Horizont Sport Business in 2003 showed that Wladimir Klitschko had been recognized by 91.7% of Germans, making him the fourth most recognized athlete in Germany at the time, while the survey conducted by Celebrity Performance Index and Respondi AG in 2013 ranked the Klitschkos #3 on the ranking of the most popular athletes in Germany behind Sebastian Vettel and Franck Ribéry. Wladimir’s world heavyweight title defense against Eddie Chambers in March 2010 drew bigger viewership numbers on RTL than the return of the Formula One legend Michael Schumacher.

After winning two minor bouts in Germany and enlisting the services of legendary boxing trainer Emanuel Steward, Klitschko again fought for the vacant WBO title on 10 April 2004, in Las Vegas, against Lamon Brewster. Klitschko dominated Brewster through the course of the first four rounds, sending him to the canvas in the fourth; however, things turned around in the fifth when Klitschko began tiring and Brewster’s punches began backing him up. Not defending himself and leaning into ropes for support, Klitschko took a standing eight count. On unsteady legs, Klitschko fell to the canvas after the bell and the referee stopped the fight for his safety.

On 22 April 2006, in Mannheim, Germany, Klitschko faced Chris Byrd for a second time, this time for the IBF heavyweight title. At the time of the bout, Byrd was ranked as the best heavyweight by The Ring, while Klitschko was ranked eighth. Coming into the fight, Klitschko was viewed as the favorite. Many observers expected Klitschko to dominate Byrd similarly to their first bout.

He made his first title defence on 11 November 2006, defeating then-undefeated heavyweight contender Calvin Brock. The fight took place at Madison Square Garden. In the opening rounds, Brock’s economical but effective movement made Klitschko reluctant to throw punches, with Wladimir not being able to fully establish his rhythm. In between the third and fourth rounds, Klitschko’s trainer Emmanuel Steward urged Wladimir to press the action. Klitschko started fighting more aggressively, hurting Brock several times with the right cross. In the fifth round, Brock opened a cut under Klitschko’s left eye that started bleeding heavily in the sixth. In the seventh round, Wladimir caught Brock with a counter right hand before sending him to the canvas with another straight right. Brock was able to get up but was unsteady on his feet, prompting the referee to stop the bout.

During Klitschko’s reign as world heavyweight champion, his biggest fights drew as many as 500 million viewers worldwide. Klitschko has been named multiple times among the 100 most influential people in Ukraine by Korrespondent: he was ranked #95 in 2006, #88 in 2010, #43 in 2011, #51 in 2012 and #45 in 2013. Forbes named Klitschko the most popular celebrity in Ukraine in 2015, placing him ahead of a singer Svyatoslav Vakarchuk and Kvartal 95 Studio, and ranked him second and third in 2012 and 2013 respectively (the ranking wasn’t conducted in 2014).

Klitschko then defeated mandatory challenger Ray Austin on 10 March 2007, at the SAP Arena in Mannheim, Germany by a second-round KO with four consecutive left hooks to Austin’s head. Klitschko did not throw a single right hand in that fight.

Klitschko then avenged one of his previous losses as he defeated Lamon Brewster on 7 July 2007, in Cologne, Germany. Brewster’s corner asked the referee to stop the fight at the end of the sixth round. It was later revealed that Klitschko fought most of the fight with a broken middle finger on his left hand.

By the end of October 2007, Wladimir Klitschko started negotiations with then-WBO world heavyweight champion Sultan Ibragimov about the unification showdown in the near future. This would be the first heavyweight unification fight since 13 November 1999 when WBC champion Lennox Lewis defeated then-WBA and IBF champion Evander Holyfield. On 20 November, Klitschko and Ibragimov officially signed the contract for their unification clash to take place on 23 February 2008 at Madison Square Garden. Two days later in Moscow, a first pre-fight press-conference was held. Klitschko began his preparations for the fight on 18 December. His training camp was located between Santa Monica, Los Angeles and Palm Beach, Florida. Ibragimov began his preparations for the bout on 25 December. Among Ibragimov’s sparring partners were Klitschko’s former opponent Jameel McCline and Swedish heavyweight prospect Attila Levin.

On 12 July 2008, at the Color Line Arena in Hamburg, Klitschko faced mandatory challenger Tony Thompson. The fight took place at the Color Line Arena in Hamburg, Germany, the same venue where Thompson had defeated then-highly regarded German boxer Luan Krasniqi in a WBO world heavyweight title eliminator almost a year prior. In the build-up to the fight, Klitschko praised Thompson for his defensive abilities, while Klitschko’s trainer Emmanuel Steward described Thompson as “one of the most difficult fights we will have”. In the pre-fight interview, Thompson promised that he wouldn’t run away from Klitschko, and would stand in front of him and fight toe-to-toe. Being 6 ft 5 in tall with 81½ in reach, Thompson was of similar height and reach as Klitschko. Many observes predicted Thompson to be a tough challenge for Klitschko, expecting Klitschko to ultimately win by TKO in the second half of the fight before the fighters would enter the championship rounds. Coming into the fight, Klitschko weighed in at 241 pounds, 6.5 lbs lighter than Thompson.

Klitschko was scheduled to defend his titles against Alexander Povetkin later in 2008, but on 25 October, Povetkin withdrew from the fight due to an ankle injury. Instead, Klitschko faced Hasim Rahman on 13 December 2008 and won by TKO. This was the third time Klitschko fought at the SAP Arena in Mannheim, Germany. He dominated the fight, winning every round while making good use of his left jab. Rahman seemed unable to withstand the Klitschko’s punch power. In the sixth round, Klitschko knocked Rahman down with a series of left hooks, leaving Rahman visibly disoriented. Between the sixth and seventh rounds, the referee warned Rahman he’s going to stop the fight if Rahman continues absorbing punishment without firing back. The referee ultimately called a stop to the contest in the 7th round after Rahman failed to respond to a series of shots. At the time of the stoppage, Klitschko was leading on all three judges scorecards, respectively 60–53, 60–53, and 60–47. According to CompuBox, Klitschko landed 194 punches (50.4% accuracy) to Rahman’s 35 (16.8% accuracy), a nearly six-fold disparity.

Klitschko is also a passionate golfer and was seen playing in the Alfred Dunhill Links Championship in Scotland. The tournament was played over three courses in 2008 including St Andrews, Carnoustie, and Kingsbarns in Fife and Angus. Klitschko was named curator of the Ukrainian pavilion at the 2009 Venice Biennale.

In 2008, after Wladimir’s photo session held for Vanity Fair magazine with Karolína Kurková, she claimed to have had a relationship with the boxer.

Klitschko was scheduled to face David Haye on 20 June 2009, but Haye pulled out within weeks of the fight complaining of a back injury. Immediately after news about Haye’s injury broke into public, a handful of heavyweight fighters, such as Alexander Povetkin, Chazz Witherspoon, James Toney, Odlanier Solis, Dominick Guinn and Eddie Chambers, expressed their interest in replacing Haye for the Klitschko showdown. Instead, Klitschko’s team started negotiations with Ruslan Chagaev, who was ranked third best heavyweight in the world by The Ring, and WBA world champion Nikolai Valuev, who was regarded as a big draw in Germany at the time. Ultimately, Klitschko reached agreements with Chagaev who agreed to step in for Haye as a last-minute replacement (Valuev’s team wanted the fight to be postponed until autumn of that year). Some observes believed that Chagaev was a better challenege for Klitschko than Haye, given his position in the ranking and the fact that, alongside WBO and IBF world titles, vacant The Ring world heavyweight title was also on the line. In the pre-fight comparison, The Ring was giving Klitschko an advantage in power, speed and athletic ability, as well as experience, while also crediting Chagaev for having better defense, praising him for his fundamentals and footwork. In terms of technique, both fighters were described as of equal level.

On 9 December 2009, Klitschko’s management group, K2 Promotions, confirmed that a bout with Eddie Chambers had been agreed to take place in Germany on 20 March 2010. This mandatory title defense, originally scheduled for December 2009, had to be delayed due to a hand injury that Klitschko sustained in training that required surgery. In the build-up to the fight, Klitschko described Chambers as “the best American heavyweight right now”. In the pre-fight comparison of the fighters, The Ring gave Chambers the upper hand in speed and athletic ability, as well as defense, while crediting Klitschko as more powerful and experienced. In the United States, the bout was not televised by any TV station but was aired on the Klitschko’s official website for $14.95 instead. The official venue was the multi-functional football stadium ESPRIT Arena in Düsseldorf, Germany.

From 2009, Klitschko was in a relationship with American actress Hayden Panettiere. Panettiere has appeared ringside at some of Klitschko’s fights, including at Klitschko’s 10th-round KO victory over Samuel Peter. The couple had a brief split in 2011, but were together again in 2013. In October 2013, Panettiere confirmed that she and Klitschko were engaged. They have one child together, a daughter, born in December 2014. In August 2018, according to Panettiere’s mother, Lesley Vogel, the couple had split for a second time. They were said to be on ‘good terms’ for the sake of their daughter.

Following the match with Chambers, a unification fight between Klitschko and David Haye, who, as of May 2009, had held the WBA title, appeared to be in the offing. Klitschko called out the Briton on YouTube in April 2010, stating, “I want to send this message to boxing fans and directly to David Haye. David, you’ve bitched out on fighting both Klitschko brothers twice already and now’s the time to make it happen. On behalf of the boxing fans around the world, I am officially calling you out to fight me. You can’t run away from me forever and you need to follow through with this fight if you want to be respected. I’m ready. What’re you waiting for?”

Haye’s trainer, Adam Booth, indicated that Haye would be willing to accept the challenge. Both sides began negotiations for a potential fight and the bout was targeted for September. As the negotiations continued to move forward, the unification fight between Klitschko and Haye was expected to take place in Germany rather than England. The IBF set a deadline to end negotiations on 17 May. A few days before the deadline, Haye said he was interested in fighting the older Klitschko, Vitali, rather than Wladimir. The fight did not materialize and Klitschko was set to take on mandatory challenger Alexander Povetkin. On 17 May 2010, the 30-day period of negotiation began for Klitschko to defend his championship against Povetkin. Within this period, discussions to make a fight with Haye were still ongoing.

The bout between Klitschko and Povetkin was initially tentatively scheduled to take place in Frankfurt, Germany, on 11 September 2010. In July 2010, it was confirmed that the bout would be taking place in Frankfurt, with Samuel Peter replacing Povetkin for the scheduled fight as Povetkin failed to show up to the press-conference, deciding to pull out of the fight at the advice of his coach Teddy Atlas who believed Povetkin was not ready to face Klitschko. Klitschko faced Peter for the second time, as they had fought in 2005 previously. Peter weighed in at 241 pounds, two pounds lighter than their first fight. Klitschko came in at a career heavy of 247 pounds.

On 5 January 2011, it was announced that Derek Chisora would get his fight with Klitschko. This enraged David Haye’s trainer Adam Booth, who described the move as a “disgrace” on a heated live phone-in with Sky Sports News. Booth alleged Haye had met every single one of Klitschko’s demands. The fight against Chisora was rescheduled for 30 April 2011 and was going to take place in SAP Arena, Mannheim. However, on 4 March, it was announced that Klitschko had pulled out of the fight due to not being fully recovered from a torn abdominal muscle. On 5 March, it was instead announced that the highly anticipated fight against Haye would take place on 2 July 2011. The fight was contingent on Klitschko’s recovery from a torn abdominal muscle. The contract was written so that if Klitschko was not fully healed, then Haye would fight his brother, Vitali.

Klitschko fought Haye in a heavyweight unification fight for the WBA (Super), IBF, WBO, IBO, and Ring magazine heavyweight titles. The fight took place at the Imtech Arena in Hamburg, Germany on 2 July 2011. Klitschko and Haye agreed to a 50–50 split of the purse and Haye was allotted 7,000 seats at the venue. Klitschko won by UD, the three judges scored it 117–109, 118–108, and 116–110 all in favour of Klitschko. According to CompuBox, Klitschko landed 134 punches of 509 thrown (26.3% accuracy), while Haye connected on 72 shots out of 290 (24.8%). Klitschko outlanded Haye in every round but fourth. Haye revealed afterwards that he had a broken toe on his right foot, and claimed that it had hindered his game plan for the fight as he felt he was unable to jump out at Klitschko like he had previously in his career. Haye was subject to much derision and ridicule from within the boxing community and fans after citing his toe as part of the reason why he lost. Despite this Klitschko claims that Haye was unable to fight because he was just too good for him.

On 6 October 2011, Klitschko announced his next fight. It was originally to be on 10 December 2011 against the former two time unified cruiserweight world champion, Jean-Marc Mormeck (36–4, 22 KOs). The fight would have taken place at Esprit Arena, Düsseldorf. It was to be Klitschko’s first title defence of his WBA (Super) title that he won against David Haye. However, on 5 December 2011, the fight was cancelled because Klitschko checked into a hospital to have a kidney stone removed. After the removal operation he suffered from fever and inflammation. The fight was rescheduled for 3 March 2012, with Klitschko dominating and knocking out Mormeck in the fourth round. CompuBox showed that in the 10 minutes and 12 seconds the fight lased, Klitschko landed 39 of 135 punches thrown (29%) and Mormeck landed just 3 of 19 thrown (16%). Mormeck failed to land anything in rounds 1 and 4.

There was first mention of a potential Klitschko vs. Mariusz Wach (27-0, 15 KOs) fight in August 2011 when Klitschko’s team approached Wach’s promoters for a fight, however nothing materialized. Wach’s promoter Global Boxing stated that it was Klitschko’s advisor Shelly Finkel that contacted them. Bernd Boente denied these claims. In August 2012, serious negotiations took place for the fight. A date in November was considered with the venue likely to be in Hamburg, Germany. Terms were fully agreed within days of the negotiations for the fight to take place 10 November. Klitschko revealed he would train with Johnathon Banks due to Steward recovering from a bowel operation. On 25 October, Steward died at the age of 68. The fight was the first time in his 16-year professional career that he had faced an opponent taller than himself. At 2.02 metres tall, with a reach of 2.08 metres and weighing 251 pounds, Wach was four centimetres taller than Klitschko with a reach two centimeters longer. In Poland, the fight was available via pay-per-view platform on Canal+ Sport for 39 zł and Polsat Sport for 40 zł.

On 4 March 2012, Klitschko stated that he would next fight his mandatory challenger Tony Thompson (36–2, 24 KOs) in a rematch from their first fight in 2008. At the time, he stated that the newly opened Barclays Arena in New York were interested in showcasing a Klitschko brother. Since they last fought, Thompson recorded five straight wins, all by KO. A purse bid was set by the IBF, where Klitschko, upon request, would receive 85% of the purse split, compared to the usual 75%. The fight was confirmed to take place at the Stade de Suisse in Berne, Switzerland on 7 July. In an interview, Klitschko admitted that Thompson was not his first choice and that he would have rather fought someone he had not fought before. “So far I’ve always been better in rematches. However, I must not take this lightly as Thompson knows me better than any other fighter”, Klitschko said in the build-up to the fight. “I’ve been waiting for this rematch for so long”, Thompson said during one of pre-fight press-conferences, “In Bern, I’m gonna finish what I’ve started 4 years ago – knock Klitschko out and take the belts back to the United States”. Thompson weighed in at 244.75, dropping 10.75 lbs from his last fight, while Klitschko weighed in at 249, the heaviest in his entire career. The additional weight appeared to be muscle.

On 29 March 2012, during a charitable auction in Kyiv, Ukraine, Klitschko auctioned off his 1996 Olympic gold medal to a buyer who bid $1 million. Klitschko said he would use the money to help the dreams of hundreds of thousands of Ukrainian children. After the sale, the buyer immediately returned the medal out of respect for Klitschko and because he wanted it to remain with the Klitschko family.

On 5 March 2013, K2 Promotions announced that Klitschko would fight another undefeated contender, Italian Francesco Pianeta, on 4 May at SAP Arena in Mannheim, Germany. Klitschko had received criticism in regards to past opponents. Pianeta was no different. Speaking to ESPN, he said, “I’m getting always criticised with my opponents, it doesn’t matter are they well known or not so much and it’s always very difficult to fight against someone that is not known because you are always getting these critics.” Pianeta said it was the biggest experience of his life, but not his biggest fight. He went on to say he won his biggest fight against cancer in 2009. From the start, Klitschko systematically broke down the Italian, consistently landing flush straight right hand shots. He dropped Pianeta with a right hand in round four, a left hand put Pianeta down in the fifth; the fight ended at 2:52 in round six when Klitschko put Pianeta down for the third time. According to CompuBox Stats, Klitschko landed 116 of 277 punches thrown (42%) and Pianeta landed 24 of 104 thrown (23%), an average of 4 punches landed per round.

The fight took place on 5 October 2013 at the Olympic Stadium in Moscow. The bout was marred with over 160 clinches, most initiated by Klitschko, followed by several repeated roughhouse tactics throughout the match. This included Klitschko’s leaning on his opponent and pushing his head down and throwing Povetkin away to prevent Povetkin from clinching, which resulted in the referee scoring some of Povetkin’s fallings as knockdowns, as well as Povetkin’s punching after the referee’s break command and leaning his head too low. Klitschko won by UD, scoring a knockdown in round two from a quick left hook, and three knockdowns in round seven, including one prompted from a straight right hand. All theee judges scored it 119–104 on the scorecards. Klitschko landed 139 of 417 punches (33%) and Povetkin connected on 59 of 283 (21%). After the fight, Klitschko told in the interview that he had little desire to go for the knockout as the Russian crowd would be disappointed, which lead to speculations about the alleged agreement between the champion and organisers to let the bout go the distance, which Klitschko later denied. With 9.2 rating, the fight became the most popular sporting event on Russian television in 2013, as well as the most watched TV programme of the year in Moscow with 13.9 rating, surpassing the Moscow Victory Day Parade. Overall, the fight was watched by 23 million people in Russia. The fight also became the most popular TV programme of Ukrainian television in 2013 with 19.5 rating and 23 million total viewers and the most watched programme of RTL Television in 2013, averaging 11 million viewers.

In November 2013, Alex Leapai (30–4–3, 24 KOs) caused a huge upset in defeating then-unbeaten Denis Boytsov to become the WBO mandatory challenger. On 5 January 2014 K2 Promotions announced that a deal was close to being reached for the Klitschko vs. Leapai fight to take place in Germany on 26 April. Klitschko signed the contract on 3 February. It was revealed that former world title challenger David Tua declined a ‘lucrative offer’ to spar with Klitschko ahead of the fight. Tua told Australian newspaper The Courier-Mail he “didn’t want to help anyone beat a ‘Samoan brother'”. On fight night, Klitschko knocked Leapai down three times, and referee Eddie Cotton stopped the fight with 55 seconds remaining in the fifth round. Despite all the pre-fight trash talk done by Leapai, Klitschko told him, “You have truly a lionheart. You never stopped. You were challenging, you were bold. You had great desire to become a champion. Not many of my opponents have that type of attitude, that type of heart.” Klitschko landed 147 of 396 punches thrown (37%), while Leapai landed a dire 10 of his 69 (14%). The 10 punches landed were made up of 6 jabs and 4 power punches.

On 6 December 2013, Klitschko and his fiancée Hayden Panettiere visited the Euromaidan-protests in Kyiv. His brother Vitali was one of the leading figures of these protests. He and his fiancée addressed the crowds.

The IBF finally ordered Klitschko vs. Kubrat Pulev on 8 May 2014 and gave a 30-day negotiation period. Klitschko’s manager Bernd Boente stated that a potential fight with WBC champion Bermane Stiverne was their main priority, a fight which would see all of the heavyweight belts at stake. Kalle Sauerland stated that he would request to get Klitschko (62–3, 52 KOs) stripped of the IBF title if he didn’t fight Pulev. At the same time Deontay Wilder was named as Stiverne’s mandatory and the WBC stated he must fight Wilder next. With the IBF purse bid split being 75–25 in favour of the champion, Klitschko requested the split be 80–20 in his favour. The IBF accepted the request. A purse bid took place on 17 June, which was won by K2 Promotions. The winning bid was $7.25 million. Sauerland Event put in a bid for $5.29 million. As per the bid, K2 had the location set as the O2 World Arena in Hamburg, with a possible date being 6 September 2014. In August, Klitschko suffered a bicep injury, thus postponing the fight by at least two months. A new date of 15 November was set. HBO announced that they would air the fight live in the afternoon, making it the 19th Klitschko fight they would show. Two days before the fight, it was revealed only the IBF title would be at stake for Pulev, however if Klitschko loses, the remaining titles would be vacated. The fight’s worldwide audience was estimated to be 300 million viewers.

On 20 January 2015 ESPN reported that the potential Klitschko vs. Jennings was confirmed and to take place on 25 April 2015 at Madison Square Garden. Negotiations initially started in November 2014. Klitschko’s manager, Bernd Boente finally announced the fight and said all contracts had been signed. The Barclays Center in New York City was originally chosen to stage the fight, but no reason was given for the change of venue.

Klitschko was scheduled to take on undefeated heavyweight contender Tyson Fury, the WBO mandatory challenger, on 24 October 2015. On 25 September 2015, Klitschko postponed the fight, citing a calf injury. It was rescheduled for 28 November 2015. On the night of the fight, there was much controversy, first starting with the gloves, then there was a complaint about the ring canvas. Klitschko reportedly had his hands wrapped without a representative of Fury present, so had to do them again. Klitschko lost the fight by UD, with scores of 115–112, 115–112, and 116–111 all in favour of Fury. It was the first defeat Klitschko had suffered in over ten years and marked the end of the so-called ‘Klitschko Era’, referring to the time period where both Klitschko brothers dominated the division. Klitschko and Fury showed little offence during the twelve rounds, but Fury did enough to take the decision. Klitschko landed 52 of 231 punches thrown (22.5%) and Fury landed 86 of 371 thrown (23.2%).

The fight averaged 659,000 viewers on Showtime in the United States. It was shown live and the fight began around 5 p.m. ET and 2 p.m. PT. Nielsen Media Research revealed the fight peaked at 687,000 viewers which was during rounds five and six. The delayed tape-replay on HBO was watched by an average 738,000 viewers and peaked at 890,000. In a press release, German TV channel RTL announced the fight was watched by an average 10.43 million viewers. The whole card averaged 9.59 million viewers. This was higher than the 8.91 million that tuned in to watch Klitschko vs. Fury in 2015. The fight did lower numbers than Klitschko’s win over Mariusz Wach in 2012, which was watched by 11 million and Klitschko vs. Haye, which was seen by over 16 million.

Klitschko was entitled to a rematch with Fury as part of the contract for their first fight. The rematch was eventually announced on 8 April 2016 and set to take place in Fury’s home town at the Manchester Arena in Manchester, England on 9 July 2016. However, Tyson Fury announced via a YouTube video that the fight would be postponed due to an ankle sprain he had received during training. He apologised to his fans and confirmed the fight would be rescheduled for a later date. On 7 July, Fury announced via his Twitter account that the rescheduled fight would take place on 29 October at the Manchester Arena. On 23 September, Fury again postponed the fight after being declared “medically unfit”, before eventually vacating the WBA (Super), WBO, and IBO titles, citing problems with depression after testing positive for cocaine. The rematch with Klitschko was cancelled as a result.

Days after the Fury rematch was called off, Klitschko was approached by Eddie Hearn, promoter of IBF champion Anthony Joshua, to fight on the 28 November date they had set for a second defence. Terms seemed to have been agreed for a £30m fight showdown although an initial contract was yet to be signed. After Fury gave up his world titles, it was said that Klitschko wanted the WBA (Super) title up for grabs in the potential match up against Joshua and waiting for approval, which the WBA kept postponing. A reason as to why the WBA was delaying sanctioning the fight was due them having a legal settlement with Lucas Browne so he could fight for the vacant title next. Klitschko then turned his attention to fighting Browne instead on 10 December, a date his team had an arena set for in Germany. On 24 October, Klitschko suffered a minor calf injury which would rule him out until 2017. Talks between the Klitschko camp and Hearn remained active with a fight set for the first part of 2017. On 2 November, the WBA finally agreed to sanction a fight for their super title as long as Joshua defeats Eric Molina in December 2016.

On 10 December, immediately after Joshua had defeated Molina at the Manchester Arena, Klitschko was invited into the ring by Hearn. It was announced that Klitschko and Joshua would face each other for the WBA (Super), IBF and vacant IBO titles at Wembley Stadium, London, on 29 April 2017. WBA president Gilberto Jesus Mendoza confirmed that the winner will have to face mandatory challenger Luis Ortiz next, with deadlines due to be set after the unification fight. A day later the IBF announced the winner must fight their mandatory challenger Kubrat Pulev. Because of this clashing with the WBA enforcing their mandatory, it was believed that either Joshua or Klitschko would have to vacate a title. In January 2017, Eddie Hearn announced that over 80,000 tickets had been sold, a new box office record, overtaking Carl Froch vs. George Groves II. He put a request in for 5,000 more tickets to be made available. At the weigh in, Klitschko weighed in at 240 and a quarter pounds, the lightest he has weighed since 2009. Joshua came in heavier at 250 pounds.

On 7 June 2017, the IBF granted Joshua an exception for him to rematch Klitschko instead of fighting mandatory challenger Kubrat Pulev. At this point, it was not said that the rematch would take place. Klitschko said he needed time to review his situation before agreeing to a rematch. It was only weeks after the fight, when Eddie Hearn filed the paperwork to the IBF to request the exception to the mandatory defence. The IBF explained that the rematch must take place no later than 2 December 2017 and the winner must fight Pulev next with no exceptions.

On 11 July 2017, Eddie Hearn traveled to the US to apply for a Nevada boxing license for promoting and to also scout potential locations in Las Vegas speaking to MGM. He had a tour of the T-Mobile Arena. Although Nigeria, Dubai and China were discussed, Hearn warmed up to the idea of the fight taking place in Las Vegas. Hearn told Sky Sports, “We met with Richard Sturm and the team at MGM in Las Vegas yesterday and had a full tour of the T-Mobile Arena which is very impressive. There is a huge appetite from both sides to hold the rematch there and we will be talking further over the next week or so to see if that can become a reality.” Showtime’s Stephen Espinoza said a deal could be reached quickly, as he was also eager to get Joshua, who has a contract with Showtime, to fight in US, “It’s no secret we’ve been salivating about getting him over here and certainly that would be a phenomenal fight. It would be the biggest heavyweight Vegas fight in probably a couple of decades, so we would love to host it.” On 25 July, Hearn pencilled on 11 November 2017 for the rematch to take place at the T-Mobile Arena. It was reported the fight could be pay-per-view in the US.

On 3 August 2017, Klitschko announced on his official website and social media channels that he was retiring from boxing. He ended his professional career with 64 wins in 69 fights, 53 by knockout. He competed in 29 world title fights.