In August 2000, he moved to Wigan Athletic, after manager Bruce Rioch bought the striker for £350,000. He scored six goals in 36 appearances in 2000–01, helping the "Latics" into the Second Division play-offs, where they were beaten by Reading at the semi-final stage after losing 2–1 at the Madejski Stadium. He scored just three goals in 17 games in 2001–02, whilst picking up seven yellow cards and one sending off. Wigan won promotion at the end of the 2002–03 season under Paul Jewell's stewardship, though Ashcroft did not feature in any league games at the JJB Stadium. He instead joined Port Vale on loan in October 2002. After four appearances for Brian Horton's "Valiants", he moved on to Huddersfield Town in December of the same year, again on loan. Huddersfield were so short of funds at the time that the loan could only go through when a wealthy supporter agreed to pay Ashcroft's wages. He appeared four times in the Second Division under Mick Wadsworth, before returning to Wigan, where he was released in February 2003. Later in the month he moved down to non-league Southport, taking up the role of player-coach at the age of 30. He scored twice in eleven Conference games, as the "Sandgrounders" were relegated at the end of the 2002–03 season. In March 2004, Ashcroft signed for Chorley on loan, where he scored three goals in eleven appearances in the Northern Premier League First Division. He later moved on to Kendal Town, where he scored 23 goals in the 2004–05 season.