The 2008–09 Toronto Raptors season is the 14th season of the franchise in the National Basketball Association (NBA). Before the season began, six-time NBA All-Star and center Jermaine O'Neal was acquired to complement Chris Bosh in the frontcourt. 17 games into the season, head coach Sam Mitchell was fired and replaced by Jay Triano. The Raptors went into the All-Star break 13 games under .500, and O'Neal was traded to Miami for Shawn Marion. The Raptors continued to struggle, and were eliminated from the playoff race with seven games of the regular season remaining.

Seeking to improve its rebounding and interior defence, Toronto traded T. J. Ford, Radoslav Nesterović, Maceo Baston, and the draft rights to Roy Hibbert to the Indiana Pacers in return for six-time NBA All-Star Jermaine O'Neal and the draft rights to Nathan Jawai. With Ford gone, virtually all the point guard responsibilities rested on José Calderón's shoulders, who re-signed to a multi-year contract. The Raptors then signed free agents Hassan Adams, Will Solomon and Jamal Sampson, but Sampson was waived at the end of the pre-season. The Raptors also signed Roko Ukić who was drafted in the 2005 NBA draft, and lost Carlos Delfino and Primož Brezec to free agency. O'Neal's arrival, however, was dwarved by the Elton Brand signing pulled off by division rivals Philadelphia. In a pre-season poll, more than half of the general managers predicted the acquisition of Brand to be the most significant one in the league, whereas the 30-year-old O'Neal was perceived to be past his prime. Nevertheless, the prospect of Toronto deploying two proven big men at the post with some of the league's best three-point shooters waiting at the perimeter signalled a change in game plan from the previous campaign.

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