He first scored for York with the second goal of a 2–2 draw away to Bradford City on 2 March 1996. This proved to be his only goal in the 1995–96 season, in which he made 17 appearances. Having failed to score in 22 appearances for York in 1996–97, Cresswell joined Third Division club Mansfield Town on loan on 27 March 1997, making his debut in a 0–0 draw away to Exeter City on 29 March. He scored his first and only goal for Mansfield in a 1–0 win away to Rochdale on 5 April 1997, before finishing the loan with five appearances. He scored four goals in 30 appearances for York in 1997–98, and during this season he was barracked by a small section of the York support. Cresswell admitted he had not made the impact he had hoped to in the York first team, but ahead of 1998–99 said "I've had some stick from a small number of fans, but hopefully I can prove them wrong. I will prove them wrong. This a big season for me. I want to do it for York City. I want to do it for myself." After a positive start to the season, Cresswell attracted attention from other clubs, with a number of scouts attending matches to watch him play. Manager Alan Little claimed some clubs were making illegal approaches for the player, and that this was having a detrimental effect on his performances. Preston North End manager David Moyes claimed his club had a bid of more than £500,000 for Cresswell rejected, while York chairman Douglas Craig rejected this, saying a formal offer had not been received from any club. He was York's top scorer in 1998–99 with 19 goals from 42 appearances. He moved to Premier League club Sheffield Wednesday on a four-year contract on 25 March 1999, with the £950,000 fee being the highest received for a York player. On his transfer, Cresswell said: "This move is no disrespect to York, it's just that I have always wanted to play at a much bigger club and as high as possible". Manager Danny Wilson described Cresswell as "one for the future" after admitting the player "is not the striker people may perceive as the big one we were chasing". His debut came in Wednesday's 2–1 home defeat to Coventry City on 3 April 1999, before scoring his first goal with an 87th-minute winner at home to Liverpool in a 1–0 win on 8 May. He finished 1998–99 with one goal in seven appearances for Wednesday.