 Ashford began his career as a trainee at Southampton, making his first team debut for the Saints in a League Cup game on 26 September 2000 against Mansfield Town.He did not last the first 45 minutes as he received a knock and was stretchered from the field.Saints manager Glenn Hoddle was quoted as being an admirer of Ashford's "sweet left peg", but in March 2002, having failed to make another first team appearance, Ashford signed for Torquay United on non-contract terms.