Following Leeds' relegation into League One in 2007, he signed for Championship club Stoke City. He won promotion with them into the Premier League as Championship runners-up in 2007–08, with Cresswell scoring 12 goals. He spent one season in the Premier League with Stoke before joining Championship club Sheffield United on loan in 2009, signing permanently in 2010. United were relegated into League One in 2011, and Cresswell played in their defeat in the 2012 League One play-off Final. He was made player-coach at the club in 2012 before rejoining his first club York in 2013, initially on loan. Cresswell retired from playing later that year, before joining York's backroom staff in 2014. He had a short spell as the club's caretaker manager in 2015, and resumed his playing career in non-League football with Tadcaster Albion the following year.