A former youth trainee with Plymouth Argyle, Jon Ashton signed full professional forms at Home Park in July 1997. He went on to make 34 league outings for Argyle before being released on a free transfer. Jon then joined Exeter City in July 2000 and played occasionally in his only season with the club.

Jon made his Grecians’ debut in the opening game of the season at St James’ Park, a 2-1 defeat at the hands of Cardiff City. Although he had a run of matches he eventually lost his place and, apart from a couple of other first team opportunities, had to be content with reserve team football. After being released at the end of the 2000-01 season Jon signed for Hayes of the Conference for whom he played until March 2002. 

Jon later appeared for Dulwich Hamlet, Bodmin Town, Bridgwater Town and Paulton Rovers before retiring with an Achilles injury aged 26. He then worked in finance.