Annand began his career with Partick Thistle, where he played one game before securing a loan move to Sligo Rovers.
Annand scored the winning goal which sealed the 1993–94 League of Ireland First Division title and also the winner in the FAI Cup semi final.
In 1995 he returned to Scotland to play with Clyde where he enjoyed the best goalscoring form of his career, scoring 42 goals in 64 league matches.
He moved to Ayr United in 2000 and spent three years with the Honest Men, which included scoring the only goal, a penalty in extra-time, in the 2002 Scottish League Cup semi-final against Hibs at Hampden.
In 2004, Annand moved to Dumbarton and part-time football, and spent the latter part of 2005 with Raith Rovers, where he finished his senior career.