Boggs played in the longest game in professional baseball history as a member of the Pawtucket Red Sox in 1981 against Cal Ripken, Jr. and the Rochester Red Wings. It lasted for 33 innings over eight hours and 25 minutes. The game took place from April 18–19, 1981, at McCoy Stadium in Pawtucket, Rhode Island.” During his last year in the minor leagues with Pawtucket, he led the league with a .335 batting-average, 167 hits, and 41 doubles.

Boggs’ career paralleled that of Tony Gwynn, who also debuted (in the National League) in 1982. Boggs and Gwynn were the premier contact hitters of their era. They both won multiple batting titles—Boggs, five and Gwynn, eight—and each won four straight batting titles to join Ty Cobb, Rogers Hornsby, and Rod Carew as the only players to do so. Gwynn and Boggs each hit over .350 in four straight seasons, the only players to do so since 1931. They joined Lou Brock and Rod Carew as the only players whose careers ended after World War II who finished with 3,000 hits and fewer than 160 home runs.

A left-handed hitter, Boggs won five batting titles starting in 1983. He also batted .349 in his rookie year, which would have won the batting title, but he was 121 plate appearances short of the required minimum of 502. From 1982 to 1988, Boggs hit below .349 only once, hitting .325 in 1984. From 1983 to 1989, Boggs rattled off seven consecutive seasons in which he collected 200 or more hits, an American League record for consecutive 200-hit seasons that was later matched and surpassed by Seattle’s Ichiro Suzuki. Boggs also had six seasons with 200 or more hits, 100+ runs, and 40+ doubles. Although he would not win another batting title after 1988 (his batting title that year broke Bill Madlock’s Major League record of four by a third baseman), he regularly appeared among the league leaders in hitting.

In 1985, Boggs had 72 multi-hit games, a club record.

In 1986, Boggs made it to the World Series with the Red Sox, but they lost to the New York Mets in seven games. He holds the record for batting average at Fenway Park, at .369.

Boggs’ mother died in June 1986 in a car accident in Tampa while he was with the Red Sox. Shortly after her death, Boggs and his father bought a fish camp on U.S. 301 just south of Hawthorne, Florida, that they named Finway; his father operated it until shortly before he died. Wade and his wife Debbie have two children, Brett and Meagann.

Boggs had a power surge in 1987, setting career-highs with 24 home runs, 89 RBIs, and a .588 slugging percentage. He never hit half as many home runs in any other season.

In his 18-year major league career, Boggs recorded three five-hit games and 59 four-hit games. On June 29, 1987, he had a career-high seven RBI against the Orioles in a 14–3 victory at Fenway.

Boggs garnered non-baseball-related media attention in 1989 for his four-year extramarital affair with Margo Adams, a California mortgage broker. After Boggs ended the relationship in 1988, Adams filed a $12 million lawsuit for emotional distress and breach of oral contract. She argued that Boggs had verbally agreed to compensate her for lost income and services performed while accompanying Boggs on road trips. Boggs’ reputation was further sullied when Adams agreed to an interview with Penthouse magazine in which she discussed intimate details of her time with Boggs. While acknowledging the affair, Boggs went on the offensive in order to combat the wave of negative press, denying many of the claims made by Adams. Boggs’ rebuttal included an appearance on the ABC program 20/20 in which he presented his side of the story to Barbara Walters. In February 1989, an appeals court threw out $11.5 million of the initial lawsuit, ruling that Adams could not seek compensation for emotional distress. The remaining demand for $500,000 was settled out of court later that year for an undisclosed amount.

In 1992, Boggs slumped to .259—one of only three times in his career that he failed to reach .300—and at the end of the season, he left the Red Sox, with whom he had spent his entire career to that point. He was heavily pursued by two teams: the Los Angeles Dodgers and the arch-rival of the Red Sox, the New York Yankees. He chose the Yankees when they added the third year to the contract that the Dodgers would not offer. Boggs went on to be awarded three straight All-Star appearances, had four straight .300-plus seasons, and even collected two Gold Glove Awards for his defense.

As a baseball player, Boggs made an appearance for the professional wrestling promotion World Wrestling Federation (WWF) in 1992. He appeared in a vignette with wrestler Mr. Perfect (Curt Hennig) in which Perfect played baseball. The two remained good friends afterward; 15 years later, in 2007, Boggs inducted the late Perfect into the WWE Hall of Fame. In the DVD The Life and Times of Mr. Perfect, Boggs related how Hennig saved his life, carrying Boggs to help after he had severely cut his leg climbing over a broken barbed wire fence during a hunting trip.

In 1996, Boggs helped the Yankees win their first World Series title in 18 years, which became his only world title. In the series’ fourth game, which saw the Yankees rally from six runs down to win, Boggs was called on to pinch hit in the tenth inning and using the batting eye he was known for throughout his career, he coaxed a bases-loaded walk out of Steve Avery, which gave the Yankees the lead in a game they went on to win 8–6. After the Yankees won the series in game 6, Boggs memorably celebrated by jumping on the back of an NYPD horse, touring the field with his index finger in the air, despite his self-professed fear of horses.

Boggs recorded 2.1 innings of pitching at the Major League level. His main pitch was a knuckleball, which he used 16 times (along with one fastball) in one shutout inning for the Yankees against the Anaheim Angels in a 1997 game. Boggs recorded a strike-out pitching during that game. Boggs also pitched 1.1 innings for Tampa Bay against the Orioles in a 1999 game, allowing one run.

Boggs signed with the Tampa Bay Devil Rays for the final two seasons of his career. He hit the first home run in Devil Rays history in the 6th inning of the inaugural game on March 31, 1998. On August 7, 1999, he collected his 3,000th hit with a home run. Despite his reputation for lacking home-run power, he is one of only three players whose 3,000th hit was a home run; he was the first to make such a hit a home run. followed by Derek Jeter on July 9, 2011, and Alex Rodriguez on June 19, 2015. Boggs retired in 1999 after sustaining a knee injury, leaving with a career batting average of .328 and 3,010 hits. His last game was on August 27, 1999; he went 0-for-3 with a walk against the Cleveland Indians. Two yellow seats among the rest of the Tropicana’s blue seats mark where both historic balls landed in right field, each with a small metal plate noting it as the area that the ball landed. Due to the fact that he signed with the 1st year expansion team Devil Rays so late in his career, he is the oldest former Devil Ray in team history. (This only includes the time where they were called the Devil Rays) He was also the 1st Tampa Bay area native to play for the team.

The Tampa Bay Devil Rays retired his #12 on April 7, 2000. It is the only number to have been issued only once by the Rays.

Before his retirement, Boggs was plagued by newspaper reports that the expansion Devil Rays gave him financial compensation in return for selecting a Devil Rays cap for his plaque at the Baseball Hall of Fame, though he has denied that any such condition was part of his contract. In light of those reports (and other rumors that teams were offering number retirement, money, or organizational jobs in exchange for the cap designation) the Hall decided in 2001 to change its practice of deferring to players’ wishes regarding cap logo selection and reinforced the Hall’s authority to determine with which cap the player would be depicted. Boggs is wearing a Boston cap on his plaque.

The Boston Red Sox inducted Boggs into the team’s Hall of Fame in 2004 and his number 26 was retired during a pre-game ceremony on May 26, 2016.

Boggs was one of the baseball players featured in the classic The Simpsons episode “Homer at the Bat,” in which he was recruited as a ringer by Mr. Burns for the Power Plant’s softball team, only to later be knocked out in a bar fight by Barney Gumble. (The depicted fight was over whether Lord Palmerston or Pitt the Elder was England’s greatest Prime Minister.) Boggs appeared as himself in the Cheers episode “Bar Wars” in which he was sent to the bar as an apology by a rival bar. He was accosted by the regulars who thought he was a fake. (Cheers writer Ken Levine revealed in 2009 that Boggs had promised to bring Kirstie Alley’s panties back to spring training with him, but in fact, brought back his mistress Margo Adams’ panties instead.) In Seinfeld’s “The Chaperone,” George convinces the Yankees to switch to cotton uniforms, assuring manager Buck Showalter that the Bombers would be “five degrees cooler than the other team.” Wade Boggs was quoted as saying. “What a fabric! Finally we can breathe.”

In 2011, he also appeared in the Psych episode “Dead Man’s Curveball.” In 2015, Boggs guest starred in the Season 10 premiere (“The Gang Beats Boggs”) of It’s Always Sunny in Philadelphia, in which characters in the show tried to drink more than 70 beers while flying across country, emulating a feat Boggs once allegedly accomplished during his career. Boggs denied that the number of beers was 64, and he reportedly told Charlie Day that he drank 107 beers in a day. One of the characters in the episode confuses Boggs with Boss Hogg; another character believes that Boggs is dead.

On December 21, 2015, the Red Sox announced that they would retire Boggs’ number (26). The ceremony was held on May 26, 2016. Boggs occasionally appears in the Yankees’ annual Old-Timers’ Day, a celebration of past Yankees in which the players play a multi-inning game of baseball at Yankee Stadium.

In August 2017, Boggs served as a fill-in color commentator for some Red Sox games played in Tampa Bay and broadcast on New England Sports Network (NESN), working with play-by-play announcer Dave O’Brien.