The 1995–96 NBA season was the Bucks' 28th season in the National Basketball Association. During the offseason, the Bucks re-signed free agent and former All-Star Terry Cummings. Early into the season, they traded Todd Day and Alton Lister to the Boston Celtics for Sherman Douglas, and dealt Eric Murdock to the Vancouver Grizzlies for Benoit Benjamin. The Bucks, led by developing superstars Vin Baker and Glenn Robinson were considered a team with playoff potential. However, their struggles continued as they posted a 15-game losing streak in March. The Bucks missed the playoffs for the fifth straight season, finishing seventh in the Central Division with a disappointing 25–57 record. Baker was selected for the 1996 NBA All-Star Game.

Following the season, head coach Mike Dunleavy was fired, Lee Mayberry signed as a free agent with the Vancouver Grizzlies, Marty Conlon signed with the Boston Celtics, and Cummings and Benjamin were both released. Cummings would sign with the Seattle SuperSonics during the next season.

For the season, the Bucks added green alternate road uniforms which lasted until 1999.