DiMaio was selected 118th overall in the 1987 NHL Entry Draft by the New York Islanders but didn’t make his NHL debut until January 8, 1989 and scored his first goal five nights later on January 13 against the New Jersey Devils. In 1991-92, he joined the NHL ranks full-time. On June 18, 1992, the Tampa Bay Lightning claimed DiMaio in the Expansion Draft. In his first season with his new team, he scored 24 points. In 1993-94, he was traded to the Philadelphia Flyers. Then, in the shortened 1994-95 season, he helped the Flyers win the Atlantic Division title and reach the playoffs for the first time in six years. In the playoffs, DiMaio scored six points in 15 games as the team advanced to the Eastern Conference finals before losing to the Devils. Over the course of his career, he played for the Islanders, Boston Bruins, New York Rangers, Philadelphia Flyers, Carolina Hurricanes, Dallas Stars, and was one of the original Lightning players during Tampa’s inaugural season.