Ashley began his playing days with spells at both Sheffield United and Sheffield Wednesday. Commendably he decided to study at University rather than go for a full time football career, and turned out for Worcester City, Malvern Town, The 61 Club (Luton) and eventually Heybridge Swifts where he first played for Garry Hill.
Ashley's form at Heybridge was such that Barry Fry took him to Peterborough in December 1997 for Â£5,000, however, he failed to settle at London Road playing just 1 first team game and re-joined Hill at his new club, St Albans City after just 6 months for a Â£10,000 fee. When Garry moved on to Victoria Road Ashley eventually followed when the Saints surprisingly made him available and he was signed for a nominal fee in March 2000. He has won representative honours for the Ryman League and an FA XI in 1999 and 2001.