It was reported in July 2008 that Crawford had turned down a move to the English Championship in favour of continuing his football in Scotland. Crawford signed a two-year-deal with Scottish Second Division side East Fife a few days later. After David Baikie resigned as manager on 14 April 2009, Crawford became caretaker player/manager, and he was given the job on a permanent basis later that month. After just over a year as manager, Crawford resigned as manager of East Fife, but remained with the club as a registered player.