Born in Swindon, Wiltshire, and raised in Holmes Chapel, Cheshire,[2] Ashton spent his youth career playing at both Stoke City and Crewe Alexandra.
[citation needed] He signed scholarship forms as a 16-year-old in 2000 before making his first-team debut on 28 October as an 83rd-minute substitute in Crewe's 1–0 win at Gillingham[3] and became one of the youngest players to represent the club.
[3] His second season at the club was disrupted by injury and a temporary loss of form,[4] but in spite of this he scored ten times and began to win international honours with England at under-16, under-17, under-18 and under-19 level.
[citation needed] Ashton scored 20 times for Crewe in the 2004–05 season prior to becoming Norwich City's record signing at £3 million.
[9] Ashton joined Norwich City from Crewe Alexandra for a fee of £3 million in January 2005, breaking the club's transfer record previously held by the £1 million deal that brought Jon Newsome to Norwich City from Leeds United in 1994, although this record was later broken by the £3.5m transfer of Robert Earnshaw to Carrow Road from West Bromwich Albion.
[citation needed] Later that year Ashton scored his first and only hat trick for Norwich City against Southampton, in a 3–1 win at Carrow Road.
[12] With Norwich out of the top flight there was much speculation surrounding Ashton's future at the club, with some people believing a player with his qualities merited a place in the Premier League.
[citation needed] Many clubs, including Manchester City and Charlton Athletic, considered him; the Addicks manager, Alan Curbishley, was reportedly prepared to axe six of his players to buy the Norwich youngster.
"[20] Ashton made an impressive start to his West Ham career, making his debut in the Hammers' 3–2 victory away to Arsenal,[21] and scored some key goals in West Ham's following fixtures, including two goals in the FA Cup quarter-final against Manchester City, which was vital in continuing the team's inspiring FA Cup run in 2006.
[23] To cap off a pivotal season in Ashton's career, he scored a goal and was a thorn in the usually solid Liverpool defence in the 2006 FA Cup Final, which eventually ended (after a 3–3 draw) in a 3–1 penalty shootout victory for the Merseysiders.
[24] However, despite not participating in any intensive training before the final, Ashton declared himself fit, and duly produced one of the most impressive displays in his short time at West Ham.
[citation needed] Despite not managing to secure a place in Sven-Göran Eriksson's England squad for the 2006 World Cup, Ashton impressed sufficiently to draw praise from football pundit Alan Hansen.
[citation needed] Ashton returned to the West Ham team on 14 July 2007 in a pre-season friendly against Dagenham & Redbridge where he played for 45 minutes.
[citation needed] However, he quickly found himself back on the Hammers' burgeoning injury list after spraining his ankle in manager Gianfranco Zola's first training session.
[citation needed] On 11 December 2009, West Ham announced that Ashton had retired, aged 26, after failing to recover from a long-term ankle injury originally sustained during an international training session, in August 2006, following a tackle from Shaun Wright-Phillips.
[42] However, just a day before the match, the striker suffered a heavy tackle from Shaun Wright-Phillips which resulted in a broken ankle in training and missed out on a chance to make his England debut against Greece.
[citation needed] However, a few days later, it was announced that he had been ruled out of action for up to six weeks with a sprained medial collateral ligament, forcing him to once again miss out on making his international debut for a second time.