DeRozan played varsity basketball all four years he spent at Compton High School in California. He was dominant from the outset, averaging 26.1 points per game as a freshman. In his senior year, he averaged 29.2 points per game, was named a Parade All-American, and was invited to play at the Jordan Brand Classic, the Nike Hoop Summit, and the McDonald’s All-American game.

A five-star prospect, DeRozan was ranked third in the nation by Rivals.com. He committed to play college basketball at the University of Southern California.

DeRozan chose to stay near home with the USC Trojans rather than going to NCAA powerhouse University of North Carolina. He was the team’s standout player, scoring a career high 22 points in the Pac-10 Conference Championship, where USC defeated Arizona State. The team lost in the NCAA Tournament to Michigan State, a 2-seed. 

DeRozan started all 35 of his games at USC and was named Pac-10 Tournament MVP. He declared for the 2009 NBA Draft following his freshman season.

The Toronto Raptors selected DeRozan with the ninth overall pick. As a rookie, he played in 77 games and started 65, averaging 8.6 points per game. He was best known in his early years for his athletic ability, and he competed in both the 2010 and 2011 NBA Slam Dunk Competition during All-Star Weekend. He finished second and third in his two appearances in the competition.

DeRozan refined his ballhandling and jump shooting, and in 2013-2014 his scoring average jumped to 22.7 points per game, including a then-career high of 40 points against the Dallas Mavericks. In 2014 he was selected for the NBA All-Star Game for the first time. His partnership with Kyle Lowry, who arrived in Toronto the year before, became a driving force behind the team’s increasingly strong performances. In the 2014-2015 playoffs, DeRozan set a franchise for points in the first quarter, with 20.

In the 2015-2016 and 2016-2017 seasons, DeRozan kept improving, posting new highs for season scoring with 23.5 and 27 points per game. In 2016, when many speculated he would seek a max contract elsewhere, he affirmed his commitment to Toronto, signing a 5 year deal for less than the max without considering any other teams. He was selected for the All-Star Team in both those seasons and made the All-NBA 3rd Team in 2017. In 2018, as Toronto’s offense moved away from the isolation-heavy tactics they had used, DeRozan’s scoring dropped to 23 points per game but he posted a career high for assists with 5.2 per game. He was named to the All-NBA 2nd Team.

Despite the Raptors’ regular season success, the team lost in consecutive playoffs to LeBron James and the Cleveland Cavaliers, including a humiliating sweep in 2018. In the 2018 offseason, looking for a change, GM Masai Ujiri replaced head coach Dwayne Casey with Nick Nurse and traded DeRozan to San Antonio, bringing in Kawhi Leonard. The move damaged Ujiri’s relationship with DeRozan, who felt betrayed despite the loyalty he had shown towards Toronto, who would go on to win the 2019 NBA Finals without DeRozan.

DeRozan was an important part of the Spurs offense 2018-2019, with 22 points per game and ranking in the top 20 in the league for assists. He recorded his first career triple-double when the Spurs defeated his former team, the Raptors. The Spurs lost in the first round of the playoffs in seven games to the Denver Nuggets. DeRozan started all the games of the 2019-2020 season before it was suspended due to coronavirus.