Born in Dundalk, County Louth, Crawley began his senior career on the books at Manchester City for a short spell before returning to his hometown club Dundalk in 1997.
He won the First Division with Dundalk in 2001 and he captained the Louth club to their FAI Cup success over Bohemians in 2002.
He was also a member of Shelbourne's highly successful 2003, 2004 and 2006 League of Ireland Premier Division title winning sides.
Crawley was out of contract at the end of the 2006 season and as a result in 2007 he rejoined his hometown club who were now in the First Division and were aiming to return to Ireland's top flight.
Ironically, Crawley rejoined Shelbourne in January 2009 with the aim of winning his second successive First Division title.