Westwood began his career at Wolverhampton Wanderers as a youth trainee, making his league debut for Wolves in September 1997.
[1] During the 1999–2000 season, he formed a strong partnership with fellow centre-back Graeme Lee, making 33 league appearances as Hartlepool reached the play-offs.
[1] For the five following seasons, Westwood missed only 21 league matches as Hartlepool earned a promotion to the Second Division in 2002–03 and reached the play-offs on two further occasions.
[1] With Hartlepool leading 2–1 late into the match, Westwood conceded a penalty and subsequently received a red card for the foul.
He rejected a new deal at Hartlepool at the end of the 2004–05 season due to family reasons; returning to the West Midlands with Walsall on 1 July 2005.
Westwood join fellow Conference National side Alfreton Town on 5 July 2013, signing a one-year contract.