The 2008–09 Cleveland Cavaliers season was the 39th season of the franchise in the National Basketball Association (NBA). They finished the regular season with 66 wins and 16 losses, the best record in the NBA, which easily surpassed the previous franchise best of 57–25 from the 1988–89 and 1991–92 seasons. LeBron James won his first MVP Award and finished second in Defensive Player of the Year voting. The Cavaliers had the fourth best team offensive rating and the third best team defensive rating in the NBA. In the playoffs, the Cavaliers swept the Detroit Pistons in the First Round in four games, swept the Atlanta Hawks in the Semifinals in four games, before losing to the Orlando Magic in the conference finals in six games, despite the Cavaliers being heavily favored to beat the Magic. The Magic would go on to lose to the Los Angeles Lakers in the NBA Finals in five games. Prior to their elimination by the Magic, many had expected the Cavs to appear in the Finals, which would've also been LeBron and Kobe Bryant's first head-to-head meeting in the NBA Finals. This was the last time that James lost in the conference finals until 2023 when the Lakers were swept by the Denver Nuggets in four games.

Key dates

Offseason

On June 26, 2008, the Cavaliers acquired the draft rights to forward Darnell Jackson from the Miami Heat in exchange for the lower of the Cavaliers two second-round picks in the 2009 NBA Draft. In addition, Cleveland purchased the rights to center Sasha Kaun from the Seattle SuperSonics. On August 4, 2008, the Cavaliers signed Tarence Kinsey to a one-year contract. On August 13, 2008, the Cavaliers traded Damon Jones and Joe Smith to the Milwaukee Bucks for Maurice Williams as part of a three-team, a six-player deal among the Cavaliers, Milwaukee Bucks and Oklahoma City. On September 5, 2008, the Cavaliers signed Lorenzen Wright to a one-year contract. Second year swingman Gabe Skinner waived to make room for the acquisition.

Draft picks

Roster

Regular season

Standings

Record vs. opponents

Game log

18,624 20,562 18,150 19,923 20,562 20,562 21,965 19,842 20,562 20,562 16,911 22,076 20,562 19,763 19,753 20,562 16,237 20,562 20,562 19,133 20,049 15,550 20,562 19,200 14,899 19,155 19,136 20,562 20,562 20,562 19,600 20,562 20,173 20,562 20,562 15,121 21,297 20,562 18,997 20,632 19,596 19,911 20,562 17,461 20,562 22,076 20,562 19,763 20,562 18,165 20,562 19,800 18,076 20,562 20,562 18,399 18,797 19,639 19,600 20,562 18,624 20,562 19,060 18,422 16,317 20,562 20,562 20,562 20,562 18,348 20,562 20,562 20,562 20,562 20,173 17,461 20,562 20,562 20,484 20,562 18,165 20,562

Playoffs

Player statistics

Legend

Season

Playoffs

Awards and records

Awards

Milestones

Transactions

Trades

Free agents

March 5, 2009: Acquired Joe Smith from Oklahoma City Thunder