Career
Callachan came through the youth system at Raith Rovers. He was promoted to the first team after agreeing a full-time contract with the club as a 16-year-old in June 2010. He spent much of the 2010-2011 season in the reserves.
He did, however, make his first team league debut in the final match of the campaign, replacing teammate Iain Williamson as a 60th-minute substitute in a 3–0 defeat against Partick Thistle on 7 May 2011.
His first game in the following 2011-2012 season was in the second round of the Scottish League Cup. Raith Rovers recorded a convincing 4–1 victory over Montrose in this July 2011 fixture, with Callachan appearing as a second-half substitute.
In March 2012 he joined Musselburgh Athletic on loan until the end of the season.
