The 2005–06 Chicago Bulls season was one of mixed results. While the Bulls reached the playoffs for a second straight season, they posted a record of just 41-41 in the regular season, 6 wins fewer than they had recorded in the previous year even though the roster was mostly the same.

The Bulls did not have any picks in the 2005 draft. The core of the team remained based around Ben Gordon, Luol Deng, and Kirk Hinrich, all draft picks from the previous two years. The Bulls did not sign any household name players through free agency, but did add Malik Allen, Darius Songaila and Michael Sweetney (through the trade explained below), all of which would split time between the starting lineup and the bench. They also added Tim Thomas; however due to a clash with Scott Skiles he appeared in just 3 games for the Bulls and would eventually move to the Phoenix Suns. The Bulls also traded their once first-round draft pick Eddy Curry to the Knicks after Curry missed some of the 2004-2005 season with a heart condition. The move was met with some controversy, although it ended up resulting in high draft picks for the Bulls due to the Knicks' poor records in the coming seasons.

The Bulls did not have any draft picks in 2005.

At 41-41, the Bulls managed to sneak into the Eastern Conference Playoffs as a 7th seed. They would lose in the first round to the eventual NBA Champion Miami Heat, although they did manage to stretch the best of 7 series to 6 games, ending a season in which they played very inconsistently on a somewhat positive note. A year later, the Bulls would defeat the Heat in a sweep in the first round.

(2) Miami Heat vs. (7) Chicago Bulls

Miami won 2–1 in the regular-season series:

Last Playoffs meeting: 1997 Eastern Conference Finals (Chicago won 4–1)

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