Shikabala joined the youth academy of Zamalek SC when he was 8-years-old and made his first team appearance in a cup match early in 2002, scoring the winning goal at the age of 16. He remained with the first team squad since then but had very limited playing time and no professional contract, which is why he was able to leave Zamalek and join PAOK FC in January 2005 for no transfer fee. He enjoyed one relatively successful season with PAOK; however, despite the Greek club being adamant that Shikabla would remain at the club until the end of his contract in 2009, he subsequently returned to Zamalek for the 2006–07 season to fulfill army duty in Egypt.

When Shikabala initially returned to Egypt from Greece in January 2007, it was amidst controversy as he signed for arch rivals Al Ahly. “I wanted to return to Zamalek,” Shikabala later recalled, “but at this time they had many administrative problems and they refused to sign me.” After the transfer went viral, Zamalek chairman Mamdouh Abbas and teammate Gamal Hamza were able to convince Shikabala to return to Zamalek with the cooperation of Al-Ahly. Shikabala enjoyed a phenomenal start with Zamalek scoring once again on his second debut for the club the winner in a 1–0 match. Shika quickly carved a place for himself in Henri Michel’s starting line-up gradually replacing club legend and fans’ idol Hazem Emam. On 2 July 2007, Shikabala scored his first goal in the derby against Al Ahly in the cup final which ended 4–3 for Al Ahly.

Shikabala has been a Zamalek fan favorite and the team’s biggest star since returning to the team in 2007. The ultras adore him and the management refused numerous offers for him notably from Anderlecht and made him the highest paid player in the history of Egypt. Shikabala has been famous for lack of discipline but the management always spoiled him as the fans adore him and the entire team is built around him. But his latest act of indiscipline was against former coach and club icon Hassan Shehata when he inexplicably had an altercation with him after being substituted. Shehata decided to freeze him out of the squad and asked to have him sold immediately, though the Zamalek board has been hesitant so far and are trying to find a solution to keep Shikabala with Zamalek.

Shikabala made his international debut on 3 June 2007 in an Africa Cup of Nations qualification match against Mauritania. While he has never played a major role on the national team, Shikabala has made several appearances during key parts of Egypt’s recent history. He was part of Egypt’s squad in the 2010 African Cup of Nations, featuring in one match as Egypt ended up as winners for the seventh time and third in a row. He decided to resign from international football in 2010, citing racist insults that he had endured from Al Ahly fans during the Cairo derby and saying that he did not want to confront such situations in international games. However, on 8 August 2012, he was called up by manager Bob Bradley for friendly matches against Benin and Cameroon.

Shikabala missed the start of the 2008–09 season due to a ban by FIFA for his illegal transfer to Zamalek. He returned in late November in fine form but once again Zamalek endured an uninspiring season and finished 6th in the league. The following season was no different until Zamalek appointed Hossam Hassan in December 2009 who gradually lifted the team from obscurity into consistently challenging for trophies once again. Under the guidance of Hassan, Shikabala finally matured as a player and started to live up to his potential. Before that he was very inconsistent and despite scoring fantastic goals and making fancy dribbles, used to drift in an out of games and was largely ineffective at times.

On 27 June 2012, Zamalek had agreed to a loan offer from Italian Serie A side Napoli for 1.8 million Euros (13.5 million Egyptian pounds). The loan deal would last one year, with the option to permanently sign Shikabala after the 2012–13 season. A few days later, Napoli failed to comment on the deal and this sparked controversy. Napoli stated that they only have interest in the player but they hadn’t made a formal offer while the Napoli coach stated they know nothing about the deal. Reports in the Italian media revealed that this is just another rumour that even Italian mercato expert Gianluca Di Marzio has called it an “April fool that is two months late”. Zamalek then stated that Napoli had failed to send agent to Cairo to officially sign Shikabala on the agreed upon deadline and the deal fell through. There was still speculation over whether Napoli would send an official offer for Shikabala throughout the 2012 summer transfer window. Several reports stated that Qatari Lekhwiya SC, Saudi Al Shabab and Ittihad Jeddah, Romanian Vaslui, German VfB Stuttgart, Spanish Espanyol, Napoli and their Italian counterparts Udinese were all battling for Shikabala’s signature.

Upon his controversial return form Al Wasl, Shikabala was unable to play for Zamalek for the rest of the 2012–13 season as his loan move outside of CAF restricted him from playing again for Zamalek until the following season. On 29 March 2013, English side Nottingham Forest Club president Fawaz Al-Hasawi expressed great interest in signing the player in the summer 2013.

Even though Shikabala was unable to play for the club, the Zamalek board had demanded that he train with the team but head coach Jorvan Vieira had refused since he didn’t want someone in the team’s training “that would not be able to play.” As of 1 July 2013, Shikabala’s loan from Al Wasl would have ended, granting him the ability to play for Zamalek once more. Shikabala made his return debut on 24 July 2013 CAF Champions League match against Al Ahly in the 57th minute. He would go on to play all 6 matches in the group stage of the Champions League scoring 2 goals and assisting 2 goals. Zamalek would then participate in the 2013 Egypt Cup. Playing the full 90 minutes in all 4 matches, Shikabala would lead Zamalek to the cup title after a 3–0 win against Wadi Degla. Shikabala had 4 assists and scored 1 goal, which was the final goal of the 3–0 win in the final from a wonderfully taken free-kick from over 30 yards out, in the tournament. 10 games after returning from Al Wasl, Shikabala scored 3 goals and had 6 assists.

As the 2013–14 Egyptian Premier League season was approaching in late December 2013, Shikabala caused yet more controversy by not showing up for training and threatening to terminate his contract with Zamalek unless he was paid his late wages over the past 3 years (from January 2011 to January 2014), which all accumulated to about 5.5 million Egyptian Pounds (almost 791,000 US dollars). On 5 January 2014, Shikabala officially terminated his contract with Zamalek as the Zamalek board were unable to both pay his late wages and convince him to stay at the club. Many of the Zamalek fans were angry with Shikabala’s abrupt departure. There were many rumours however linking Shikabala to many clubs in Europe after putting fine displays for Zamalek over the years and during his loan spell at Al Wasl. After weeks of speculation between resigning for Zamalek or leaving, Shikabala, due to his love for his boyhood club, decided to sign with Zamalek and leave through the club so that Zamalek can benefit financially from his sale to help solve the financial problems the club was facing. The Zamalek board agreed to sell Shikabala at the end of the January transfer window for the proper price.

On 29 January 2014, it was announced that Shikabala signed for the Portuguese club Sporting CP for 700,000 dollars and would travel the following day to Lisbon to complete a medical and officially sign with the club. In the final hours of the January transfer window, there were several problems with the negotiations between Shikabala, Sporting, and Zamalek but with 3 minutes remaining in the transfer window, they finally agreed to a deal of 700,000 US dollars in addition to 5% of any future sale if Sporting decide to sell Shikabala to another club. Shikabala decided to wear the number 7 jersey in Sporting.

Shikabala made his first appearance for the reserve team on 16 February 2014 against Tondela. He started the match but was substituted 28 minutes into the game after picking up a minor ankle injury.

In September 2014, Shikabala went to Egypt to play for his national team, since then he did not return to Sporting or to Portugal. His salary was frozen and his house and car were taken due to lack of payments.

On 27 August 2015, Zamalek officially signed Shikabala after his unsuccessful attempt with Portuguese side Sporting. “Zamalek chairman Mortada Mansour has approved a five-season contract deal with the player,” the club’s official website stated. He was immediately loaned to Egyptian league side Ismaily SC as there was no place for the player in Zamalek’s closed squad. Following the 2015–16 season, Shikabla completed his loan and returned to Zamalek as the team captain.

After being featured in the squad for Egypt’s 2014 African Nations Championship qualifying campaign, Shikabala endured a three-year absence from the national team. He returned to the squad on 12 November 2017, where he scored his first official international goal against Ghana in Egypt’s final World Cup qualifier. In June 2018, he was named to Egypt’s final 23-man squad for the 2018 FIFA World Cup in Russia.

After a loan spell at Saudi Arabian club Al-Raed in 2017–18, Shikabala was loaned to Apollon Smyrni of the Greek Superleague in August 2018.