Released by Tottenham at under-14 level, Ashford started his senior career at Maldon & Tiptree in 2014, enjoying a number of spells at non league clubs such as Stansted, Brightlingsea Regent and three spells at Witham Town.
It was at Witham where Ashford attracted attention from National League South sides East Thurrock United and Concord Rangers, the latter of which he was still dual registered with Witham, who he would help keep up on the last day of the season after Concord were denied a shot at the playoffs.
He then made a move to Hemel Hempstead Town in May 2019, where ten goals before the curtailment of the season due to Covid attracted League Two side Crawley Town to offer a two-year deal. A successful loan move to the Cards in March 2021 saw Ashford net four times in a struggling side before he would eventually join Ayr United of the Scottish Championship in January 2022, enjoying 18 months with them before swapping Scotland for Northern Ireland in Cliftonville.
Eight goals in 29 appearances followed before a move back to England to join Wealdstone last summer, where he has netted seven times before joining the Cards ahead of an important last nine league games.