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, easily surpassing the previous franchise best of 57–25 from the 1988–89 and 1991–92 seasons.
On October 7, the Cavaliers' pre-season began with an 84–104 loss to Toronto Raptors.
On October 28, the Cavaliers' regular season started with an 85–90 loss at the Boston Celtics.
On October 30, the Cavaliers beat the Charlotte Bobcats 96–79 for their first win in their home opener.
On November 8, the Cavaliers beat the Chicago Bulls 106–97 to improve their record to 5-2 and take over first place in the Central Division.
On November 18, the Cavaliers beat the New Jersey Nets 106–82 for their then season-high eighth straight win and improved their record to a then season high seven games over .500 (9-2).
On December 3, the Cavaliers beat the New York Knicks 118–82 to set a franchise record by starting the season with ten straight home wins.
On December 9, the Cavaliers beat the Toronto Raptors 114–94 to set an NBA record by winning nine straight games by 12 or more points.
On December 12, the Cavaliers beat the Philadelphia 76ers 88–72 for their season best 11th straight win (which tied a franchise record), to improve to a then season high seventeen games over .500, their best 23 game start in franchise history (20-3), and to improve their franchise record by starting the season with thirteen straight home wins.
On December 28, the Cavaliers beat the Miami Heat 93–86 to improve to a season high 22 games over .500, their best 30 game start in franchise history (26–4), and to improve their franchise record by starting the season with 16 straight home wins.
On January 7, the Cavaliers beat the Charlotte Bobcats 111–81 for their best 34 game start in franchise history (28–6), to improve their franchise record by starting the season with 18 straight home wins, to take over first place in the Eastern Conference and to take a share of the best record in the NBA with the Los Angeles Lakers.
On January 9, the Cavaliers beat the Boston Celtics 98–83 to improve to a season high 23 games over .500, their best 35 game start in franchise history (29–6), and to improve their franchise record by starting the season with 19 straight home wins.
On January 23, the Cavaliers beat the Golden State Warriors 106–105 to improve to a season high 25 games over .500, their best 41 game start in franchise history (33–8).
On February 3, the Cavaliers beat the Toronto Raptors 101–83 to get their franchise record 23rd straight home victory, and improved to 38–9 overall on the season.
On February 8, the Cavaliers lost to the Los Angeles Lakers 91–101, their first home loss of the year, dropping to 23–1 at home and 39-10 overall on the season.
On February 10, the Cavaliers lost to the Indiana Pacers 95–96, marking their first consecutive losses of the season.
On March 2, the Cavaliers beat the Miami Heat 107–100, improving to 47-12 and marking the first time in franchise history the team was 35 games over .500.
On March 4, the Cavaliers beat the Milwaukee Bucks 91–73, becoming the first team in the league to clinch a playoff berth.
On March 13, the Cavaliers beat the Sacramento Kings 126-123, clinching the Central Division title: their first since the 1975–76 season and their second in franchise history.
On March 19, the Cavaliers tied an NBA record by committing just 2 turnovers in a 97–92 overtime victory over the Portland Trail Blazers.
On March 24, the Cavaliers beat the New Jersey Nets 98–87, improving their record to 58–13 and setting a franchise record for wins in a season.
On March 31, the Cavaliers beat the Detroit Pistons 79–73, extending their winning streak to a new franchise record 13 wins in a row, setting a new franchise record and tying an NBA record for wins in any month by improving to 16-1 in March, and extending their franchise record for wins in a season, improving to 61–13.
On April 10, the Cavaliers beat the Philadelphia 76ers 102–92, clinching the best record in the Eastern Conference for the first time in franchise history.
On April 13, the Cavaliers beat the Indiana Pacers 117-109, clinching the best record in the NBA and home-court advantage throughout the playoffs, the first time ever the Cavaliers have done so.
On April 15, the Cavaliers concluded their regular season with a 111-110 loss to the Philadelphia 76ers in OT. They finished the season 66–16, going 39–2 at home and 27–14 on the road. Their home record was the second-best in NBA history.
On April 26, the Cavaliers advanced to the second round of the 2009 NBA Playoffs by defeating the Detroit Pistons four games to none.
On May 9, the Cavaliers defeated the Atlanta Hawks 97–82 and became the first team in NBA history to win seven consecutive playoff games by a double-digit margin.
On May 11, the Cavaliers defeated the Atlanta Hawks 84–74, earning a spot in the NBA Eastern Conference Finals. It was also the first time in franchise history they swept two consecutive playoff series.
On May 30, the Cavs' season ended when they lost to the Orlando Magic in Game 6 of the Eastern Conference Finals, 103–90, in Orlando. The Magic took Game 1 in Cleveland with a 1-point victory and went on to win the series 4-2 before going on to lose to the Los Angeles Lakers 4–1 in the NBA Finals. 8 of the last 9 eastern conference No 1 seeded teams have been beaten in the Conference Finals.
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 November 18, LeBron James became the youngest player to reach 11,000 career points and the only player to score 11,000 points in a Cavaliers uniform; he also passed Jim Brewer for 6th in defensive rebounds in Cavs history.
On January 4, LeBron James passed Brad Daugherty to become the Cavaliers' all-time free throws attempted leader. On the same night he also passed Wesley Person for 2nd all time in three-point field goals made.
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