Crewe Alexandra Born in
Bridgnorth, Westwood started his career as a trainee at Manchester United and was part of the
FA Youth Cup winning side of 1995. He never made a first-team appearance for the Red Devils, but
Dario Gradi spotted the youngster's potential and secured Westwood's services for Crewe Alexandra for a
£40,000 fee. Westwood slotted in well to the
Second Division side. He played fifty games in the
1996–97 season, including the
1–0 win play-off final over
Brentford that took the Railwaymen into the
First Division. However, he was to only play 22 games in the
1997–98 season. His swansong for the
Cheshire club came on 13 April 1998, when he scored the opener of a 2–0 win over near rivals
Stoke City at
Gresty Road.
Bradford City In summer 1998, he signed with Bradford City, a tribunal later awarded Crewe a £150,000 payment from Bradford.
Sheffield Wednesday Westwood joined Sheffield Wednesday on a one-month loan in August;
Paul Jewell had switched to the Owls and took Westwood with him permanently for £150,000 in September, £100,000 less than Bradford had originally wanted. He played 38 games
that season, scoring five goals and picking up ten yellow cards. A particular highlight was scoring the winning goal as Wednesday knocked Premier League side
West Ham United out of the
League Cup. The
next season Wednesday were fighting for First Division survival and Jewell had already left for
Wigan Athletic. Westwood played 33 games, helping the club to the
League Cup semi-finals. He began to suffer from a
groin injury in October 2002, and played just 25 games in Wednesday's
2002–03 relegation season.
Northampton Town In July 2003, he signed with Northampton Town. His time at Northampton was one ravaged by injury. He played just nine
Third Division games in
2003–04, being out from September to January with a shoulder injury. He was sent off in the
play-off semi-final first leg defeat to
Mansfield Town. In July 2004, Westwood was appointed club captain. The
2004–05 season was the first season of
League Two, and Westwood could only muster 19 league appearances following his return to action in October. He signed a new contract at the end of the year, despite still suffering from damaged knee ligaments, an injury he picked up in April. Once again Northampton reached the play-offs, only to exit at the semi-final stage, this time to
Southend United. The Cobblers finally achieved promotion in
2005–06 as runners-up; Westwood played just three games all season, all as a substitute. He left
Sixfields at the end of the campaign after not being offered a new contract, and instead signed for
Mark Wright's
Chester City.
Chester City He continued to struggle with his hamstring. Though he played 25 games, he played his last in Chester colours after being injured against
Wycombe Wanderers on 13 January 2007. In March, he joined Swindon Town on loan from the remainder of
the season to provide much-needed cover for the
Wiltshire club. The season ended with Westwood playing in a centre-back partnership with
Jamie Vincent, helping Swindon to win promotion from League Two with a third-place finish. He left the club on 30 August, to join
League One side Port Vale on a temporary short-term deal. He made his Vale debut two days later in a 1–0 win at
AFC Bournemouth. He returned to Chester in December 2007, before joining Stevenage Borough on a
free transfer at the start of the 2008 January
transfer window.
Non-League He was released by Stevenage in July 2008, after making twenty appearances, scoring twice for the
Conference side. After a trial with
Lincoln City he joined Conference side
Wrexham, becoming one of the first signings of new manager
Dean Saunders, with whom Westwood played at Bradford City. He scored his first goal for the Dragons with a
header in an
FA Trophy game with Mansfield Town, to put them through to the
second round. In July 2009 he signed a contract extension, keeping him at the Welsh club for the
2009–10 season. At the end of the season, Westwood moved to
Kettering Town in order to be closer to his family. Whilst at Kettering, he was sent off twice in two games, against
Cambridge United and then
Southport. Westwood left Kettering by mutual consent in January 2011 and was granted permission to train at his former club, Crewe Alexandra. The managing staff were impressed with his fitness levels and rewarded him with a short-term contract, keeping him at the club until the end of the season. He became the second Ashley Westwood in the squad, joining
Ashley R. Westwood, 13 years his junior. He made six appearances but was not retained beyond the end of the campaign. In August 2011 he agreed to spend a month on trial at former club Northampton Town, and quickly joined the club on non-contract terms. He scored the only goal for Northampton to secure three points at
Aldershot Town on 13 August, his first start in his second spell at the club. Having made five appearances, he was given a contract lasting until the end of the year. He was released by new manager
Aidy Boothroyd in December, having played 20 games for the struggling Northamptonshire club.
Conference National side Kettering Town underwent a financial crisis in
2011–12, and caretaker manager
Mark Cooper walked out on the club on 18 January after his players went unpaid. Three days later, Westwood was announced as the club's temporary manager; he was also registered with the club as a player. Later that day, his new team lost 4–1 to
Wrexham at the
Racecourse Ground, having only been able to name two substitutes. The Poppies then won their next two games at
Nene Park to move out of the relegation zone. After being told his job was secure until the end of the season, he picked himself to play for the first time in the 1–0 defeat at
Hayes & Yeading on 10 March; also in March he signed
Ben Joyce and Max York. Kettering failed to turn things around, and were relegated in last place having conceded 100 goals in 46 league games. In May 2012, he signed a one-year playing contract with Lincoln City, also in the Conference. Lincoln manager
David Holdsworth reluctantly allowed Westwood to leave the club on 6 July 2012, having failing to kick a ball for the Imps. On 6 July 2012, just over a month after signing for Lincoln, he accepted an offer by
Michael Appleton to join the coaching staff at League One side
Portsmouth. The club's financial situation meant that he was obliged to return to playing duties in the
2012–13 campaign. However, his only appearance was in a 3–0 League Cup defeat to Plymouth Argyle at
Home Park on the opening day of the season; he was 12 years older than the team's second-oldest player
Simon Eastwood. ==Coaching career==