Career
Professional
Cruickshank began his professional career in Trinidad with Caledonia American Institute of Architects in 2006. He first moved to the Cleveland City Stars in 2007, playing in two matches and recording 18 minutes of USL Second Division play, but missed much of the season with a high ankle sprain. He returned to Trinidad in 2008, playing for Saint Ann"s Rangers and Ma Pau, before re-joining the Cleveland City Stars in the USL First Division in 2009.
International
Cruickshank has been capped four times by the Trinidad and Tobago national football team
