 Born in Stockport, Greater Manchester, Crowther spent nine years at his local club Stockport County moving through the youth system, before making his first team debut for the club on 2 January 2006 in a 2–2 draw against Cheltenham Town, where aged just 17, he came on as a substitute and was made captain, making him the youngest captain in the club's history.He went on to make one other senior appearance for Stockport before the club were approached by Liverpool requesting an opportunity to take both Crowther and Greg Tansey on trial with a view to take them to a tournament in Milan, and agreed deals with Stockport for both players subject to satisfactory performances from the players at the tournament.The players both went to the tournament and Crowther joined Liverpool on 9 July 2007, with Tansey deciding to stay at Stockport.