The Raptors entered the NBA as an expansion franchise in 1995 under original owners John Bitove and Allan Slaight, with Isiah Thomas as the team's first general manager; Maple Leaf Gardens Ltd., later MLSE, bought full control of the club in 1998. The team struggled through its early seasons before the 1998 arrival of Vince Carter, whose highlight-reel athleticism made him the franchise's first true star and helped the Raptors reach the playoffs in the early 2000s, including their first playoff series win in 2001. Carter's departure in 2004 was followed by a middling decade under general manager Bryan Colangelo, during which forward Chris Bosh briefly lifted the team back into the playoffs before leaving as a free agent in 2010.

The franchise's modern era began when Masai Ujiri took over basketball operations in 2013, building sustained playoff teams around DeMar DeRozan and Kyle Lowry that twice reached the Eastern Conference Finals. A 2018 trade brought in Kawhi Leonard, and in his lone season with the team, the Raptors won the 2019 NBA Finals over the Golden State Warriors, becoming the first and so far only team based outside the United States to win an NBA championship. Leonard left for Los Angeles that summer, and the Raptors have since moved into a rebuilding phase centered on Scottie Barnes, while ownership of parent company MLSE has consolidated toward Rogers Communications.