 Cresswell was born in Bridlington , East Riding of Yorkshire to George and Denise ( née <unk> ) . He started playing for Bridlington Rangers at the age of eight before joining the York City youth system aged 14 in 1991 . Having been top scorer for the Northern Intermediate League team for three consecutive seasons , he signed a professional contract on 15 November 1995 . Cresswell made his first team debut away to Brentford in a 2 – 0 defeat in the Second Division on 20 January 1996 . He first scored for York with the second goal of a 2 – 2 draw away at Bradford City on 2 March 1996 . This proved to be his only goal in the 1995 – 96 season , in which he made 17 appearances . 
