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.