The 1989–90 NBA season was the Bucks' 22nd season in the National Basketball Association. During the offseason, the Bucks acquired Alvin Robertson and Greg "Cadillac" Anderson from the San Antonio Spurs. Early into the season, the Bucks defeated the Seattle SuperSonics in a quintuple-overtime game on November 9, 155–154 at the Bradley Center. However, they fell under .500 along the way. Despite a season full of injuries, the Bucks won nine out of ten games between December and January, as they finished third in the Central Division with a 44–38 record. Ricky Pierce was named Sixth Man of The Year averaging 23.0 points per game off the bench, despite playing in just 59 games due to injury. However, in the first round of the playoffs, they lost to the Chicago Bulls in four games.

(3) Chicago Bulls vs. (6) Milwaukee Bucks: Bulls win series 3-1

Last Playoff Meeting: 1985 Eastern Conference First Round (Milwaukee won 3-1)

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