Westwood was selected by the Bombers in the 1991 season, when he was selected 48th overall in the 6th round of the Canadian College Draft. Westwood was also known for his mullet, which he reportedly vowed not to cut until he wins the Grey Cup. He decided to grow it out after the 2001 Grey Cup loss to Calgary, in which he missed three out of four field goal attempts. In a radio interview, he publicly denied this claim and attributed his hair to his spirituality, and resents the notion that his hair has anything to do with football. This poor performance capped off what was Westwood's worst season statistically as he only converted on 60.8% of his field goal attempts that year. After a disappointing start to the 2007 season against Edmonton, Westwood was told by Bomber coach Doug Berry not to dress for the second game of the season against Montreal. After replacement Rob Pikula went 1/2 in field goals, Westwood was reinstated as the Bomber's place kicker by the third game of the season. In the 7th game of the season however, Westwood sustained a hamstring injury and his future with the club was again in doubt. However, after injuries to Pikula and newly signed Pat Fleming, Westwood was called upon for kicking and punting duties in the Eastern Semi-Final where he went 1/2, kicking the game-winning field goal from 20 yards out with no time left on the clock. Westwood was cut by the Bombers during training camp on June 15, 2008. Westwood was re-signed by the Blue Bombers on Oct 19, 2009 to their practice roster following an injury to starting punter Mike Renaud and struggles by place kicker Alexis Serna to pull double duty. On April, 2010, Westwood was released by the Blue Bombers. He is known for stirring things up off-field: he has tried his hand at professional boxing and tap dancing, and had a public feud with Montreal AlouetteEd Philion. He is arguably most known for his tongue-in-cheek insult of the rival Saskatchewan Roughriders' fans by calling them "banjo-pickin' inbreds." He later followed that up with a faux apology, saying he did not think anyone in Saskatchewan was actually capable of playing a banjo. These quotes inspired the Banjo Bowl.
After retiring from football, Westwood was an on-air host for CFQX-FM in Winnipeg from March 2009 to March 2011. He is currently a morning host on CFRW, Winnipeg's TSN Radio station.