Career
Callahan was drafted 235th overall by the Pittsburgh Penguins in the 1992 National Hockey League Entry Draft. After spending four years at Boston College, Callahan turned pro in the summer of 1997, signing with the Hampton Roads Admirals. Callahan scored his first professional point, an assist, on October 17, 1997 against the Richmond Renegades.
Callahan assisted on the opening goal scored by Victor Gervais, scored 10:10 into the first period.
Callahan was placed on injured reserve after his seventh game with the Admirals. He finished the season with 21 points in 49 games.
In the offseason, Callahan signed with the Chesapeake Icebreakers, who were coached by former National Hockey League enforcer Chris Nilan. With Chesapeake, Callahan scored his first professional 20-goal season, scoring 20 goals in 70 games, making him one of five 20-goal scorers on the roster during the 1998-1999 ECHL season.
Callahan joined the Jackson Bandits for the 1999-2000 season, where he led the Bandits in goals (28), a career high
Callahan also finished third in team scoring with 46 points in 70 games. He also led the team with 168 PIM. Callahan would play one more season with the Bandits before retiring after the 2000-2001 ECHL season. Callahan was drafted by the Pittsburgh Penguins in the tenth round, 235th overall.