Beginning his career as a low-minute player, he gradually improved his role with the team, eventually forming a duo with his cousin Vince Carter.

His final seasons in the NBA were plagued by injuries, and he retired in 2013 following a brief stint with the Qingdao DoubleStar Eagles of the Chinese Basketball Association (CBA) and the San Antonio Spurs.

[9] A relatively unknown player coming out of Florida, McGrady made a name for himself after a strong performance at the Adidas ABCD Camp, an experience that helped him recognize his true talent.

[9] Initially, McGrady considered playing college basketball at the University of Kentucky, but he ultimately decided to enter the NBA draft as he was a projected lottery pick.

"[15] By the 1999–2000 season, the duo had developed a reputation for their athleticism, giving memorable performances at the All-Star Weekend Slam Dunk Contest.

[14] McGrady, now playing significant minutes, was a contender for the Sixth Man of the Year Award before being elevated to Toronto's starting backcourt in late March.

[18] Following Toronto's first-round exit, McGrady became a free agent and signed with the Orlando Magic on August 3, 2000, through a sign-and-trade deal that sent a future 2005 1st round draft pick (Fran Vázquez was later selected) to the Raptors.

[24] During the 2000–01 season, McGrady defied the expectations of many,[25] emerging as one of the best players in the NBA, with Milwaukee Bucks General Manager Ernie Grunfeld going so far as to call him "one of the top five talents in the league".

[31] In 2002–03, McGrady won his first scoring title and, behind averages of 32.1 points, 6.5 rebounds, and 5.5 assists per game, finished a career-best fourth in NBA Most Valuable Player Award voting.

[34] The Magic would go on to take a commanding 3–1 lead, and McGrady made headlines when he prematurely assumed that Orlando were guaranteed to advance, replying in an interview, "It feels good to get in the second round."

[21][36] Throughout the season, Orlando struggled because of a series of injuries, finishing the year with the worst record in the East despite McGrady winning his second consecutive scoring title.

[5] On June 29, 2004, McGrady, Juwan Howard, Tyronn Lue, and Reece Gaines were traded to the Houston Rockets as part of a seven-player deal that sent Steve Francis, Cuttino Mobley, and Kelvin Cato to the Magic.

[5] In response to the trade, McGrady stated that he was happy with the situation and expressed excitement over the prospect of playing alongside Rocket All-Star center Yao Ming.

[40] On December 9, McGrady had one of the most memorable performances of his career, scoring 13 points in the final 35 seconds against the San Antonio Spurs including a last-second three-pointer to secure a comeback victory.

[5] In Game 2 of the first round of the postseason, he had another signature performance, completing a "thunderous" dunk over 7'6" Dallas Mavericks center Shawn Bradley and hitting a game-winner for a 113–111 victory.

[44] Despite his health concerns, McGrady was able to play in that year's All-Star Game in front of his home crowd in Houston, exploding for 36 points in just 27 minutes.

[45] Early in the 2006–07 season, McGrady missed seven games, again because of back spasms, eventually deciding to visit a doctor and receive treatment for the injury as he felt that it was affecting his speed and explosiveness.

[46] His health issues and the ascension of Yao Ming, who was having a breakout season, resulted in McGrady temporarily becoming the team's second scoring option.

[5] In a surprise turn of events, the Rockets qualified for the playoffs without McGrady and advanced to the second round, pushing the eventual-champion Los Angeles Lakers to seven games.

[5] A free agent for the first time in ten years, McGrady met with and worked out for the Los Angeles Clippers[65] and Chicago Bulls.

[74] On April 16, 2013, shortly after the conclusion of the CBA campaign, McGrady signed with the San Antonio Spurs in time for him to qualify for their playoff roster.

[75] The Spurs eventually advanced to the 2013 NBA Finals, losing in seven games to the Miami Heat, which provided McGrady with the opportunity to play his first career postseason minutes outside of the first round.

[77] McGrady was selected to the United States men's national basketball team for the FIBA Americas Championship 2003 in San Juan, Puerto Rico.

[89][90] McGrady's playing style has been compared to George Gervin's because both players made scoring appear easy with their "smooth" approach to the game.

[91] Some analysts have remarked that McGrady's length, playmaking, and shooting abilities would have made him more effective in the modern era of basketball, and that he was ahead of his time.

[92] On the defensive side of the ball, McGrady's effort was less consistent, but he demonstrated the ability to raise his level in meaningful games, such as during the playoffs against the Mavericks, where he often drew the assignment of guarding Dirk Nowitzki.

[14] In response to these criticisms, former Rockets coach Jeff Van Gundy described McGrady as a poor practice player but praised his coachability, unselfishness, and ability to perform well in big games.

[99] Tracy's younger brother, Chancellor "Chance" McGrady, played for the 2008 NCAA Division I men's basketball tournament runner-up Memphis Tigers.

[110] In August 2021, McGrady launched an app, SOLEcial, designed to sell autographed shoes, trading cards, and other memorabilia directly to buyers.

[111] In December 2024, McGrady, his former Raptors teammate Vince Carter, Jozy Altidore and a coalition of private equity fund executives purchased a minority stake in the National Football League's Buffalo Bills.