Perry began his hockey career playing with the Brockville Braves of the Central Junior Hockey League, where he earned the team rookie of the year award in 2002-03 all-star honours in 2003-04. Perry scored 7 goals and 16 assists in 38 games with Braves. Perry was then selected ninth overall by the Sarnia Sting in the 2002 Ontario Hockey League Draft.
Perry instead chose to enroll at Boston College, where he played with the men's hockey program for 3 games in the 2004-05 season. Perry then joined the Barrie Colts of the OHL during the end of the 2004-05 season. Perry played 29 games that season, recording 8 assists. Perry played his first full OHL season in 2005-06, where he recorded 4 goals and 20 assists in 67 games for the Colts. Before the start of the 2006-07 season, Perry moved to the London Knights organization. In 2006-07, with the Knights, Perry recorded 1 goal and 18 assists in 67 games.
Perry was signed by the Columbia Inferno of the ECHL, where he began playing the first professional hockey of his career in 2007-08. In 55 games with Columbia, Perry recorded 6 goals and 22 assists. Perry was then signed by the Toronto Marlies of the AHL, and finished the 2007-08 season in Toronto, recording an assist in 8 AHL games.