Cyril Sidlow was replaced by Ashcroft in the 1951/52 season having only featured in nine first-team matches since the resumption of League football following World War II. Ashcroft earned the distinction of saving a penalty from Preston legend Tom Finney on the opening day of the 1952/53 season and was first choice until December 1952 when he lost his place to Russell Crossley after a disastrous spell for the club. The arrival of Dave Underwood in December 1953 further restricted his chances. Liverpool were relegated in the spring and South African Doug Rudham was signed at the start of the 1954/55 season. Ashcroft still managed 15 games in his final season despite battling for one position with Underwood and Rudham.
Ashcroft was signed by future England World Cup-winning coach Sir Alf Ramsey for Ipswich Town who played in Third Division South. After only seven games he broke his arm in a reserve game and left for Coventry the following summer. He only stayed at the Sky Blues for one season as his break hadn't healed properly so City had effectively signed a 'keeper who couldn't straighten his arm!