Crawford started his career with Raith Rovers, with whom he won the 1994 Scottish League Cup Final and played in the UEFA Cup. This earned him a move to English football with Millwall, but Crawford returned to Scotland after just one year. He had a mixed spell with Hibernian, suffering relegation but then winning promotion. Crawford then had the most productive spell of his career with Dunfermline Athletic, during which time he became a Scotland regular, amassing 25 caps in total. Crawford played in three Scottish Cup Finals (two for Dunfermline and one for Dundee United) in the mid-2000s, losing all three to Celtic. Crawford's stint with Dundee United came after a short-lived return to English football with Plymouth Argyle.