Dineen's was named as a player-coach during his final season with the Utah Grizzlies in 1999 until he was traded to the Chicago Wolves in March 2000. After retiring from playing, Dineen was named an assistant coach with the Louisville Panthers of the American Hockey League (AHL) in 2000–01. Louisville was the AHL affiliate of the Florida Panthers. Dineen worked under head coach Joe Paterson. The next season, he was named head coach and general manager of the Macon Whoopee of the East Coast Hockey League (ECHL) for the 2001–02 season. Under Dineen, the Whoopee finished with a 29–31–12 record, earning 70 points, and did not make the post-season. Following the season, the Whoopee relocated to Lexington, Kentucky, to become the Lexington Men O' War and he was not retained by the club.