Chelios signed another one-year contract with the Red Wings for the 2008–09 season. On December 5, 2008, Chelios played in his first of two games for the Grand Rapids Griffins, the American Hockey League (AHL) farm club for the Red Wings, as part of a conditioning stint. At 46 years of age, he became the oldest player in the 73-year history of the AHL. At the conclusion of the 2008–09 season, Chelios was a finalist for the Bill Masterton Memorial Trophy.