Cresswell was Preston's top scorer in his first two permanent seasons with Preston, scoring 15 goals in 44 appearances in 2001–02 and scoring 16 in 46 appearances in 2002–03. He was also named Preston's Player of the Year for 2001–02. He received the first red card of his career in Preston's 4–1 defeat away to Coventry on 17 March 2004 after he was judged to have kicked out at opponent player Calum Davenport, although both managers later admitted David Healy was the culprit. He scored three goals in 47 appearances in 2003–04.