Cresswell started his career with York City in their youth system, making his first-team debut in a Second Division match in 1996. Having scored 19 goals for York in the 1998–99 season, he signed for Premier League club Sheffield Wednesday in 1999. After their relegation the following year, Cresswell joined Leicester City of the Premier League, but was loaned to First Division club Preston North End in 2001 and played for them in the 2001 First Division play-off Final. He signed for Preston permanently later that year. He had four full seasons with Preston, scoring a career best 21 goals in 2004–05, which culminated in defeat in the 2005 Championship play-off Final. Cresswell signed for Preston's Championship rivals Leeds United in 2005, and endured a number of knee injuries while with them. He missed their defeat in the 2006 Championship play-off Final through suspension.