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He began his career at Nottingham Forest, becoming the youngest player ever to play for the club when he made his first team debut in October 2001 at the age of 16. He was loaned out to Lincoln City and Milton Keynes Dons in 2005, before he left the Football League to spend the 2005–06 season in the Conference with Cambridge United. He then spent three seasons with Kettering Town, helping the club to win the Conference North title in 2007–08. He signed with Notts County in May 2009, and helped the club to win the League Two title in 2009–10. He was sold on to Chesterfield in August 2011, and won the Football League Trophy with the club in 2012, scoring a goal in the final. He joined Walsall, initially on loan, in November 2012. He finished as the club's top-scorer in the 2013–14 campaign, but was released in May 2014. On 17 June 2014 Westcarr joined Portsmouth on a free transfer after leaving Walsall, penning a two-year contract.

On 17 June 2014 Westcarr signed a two-year deal with League Two side Portsmouth. Westcarr scored his first goal for Portsmouth on 19 August 2014 in a 2–0 league victory over Northampton at Fratton Park.

Westcarr scored twice in the FA Cup Fourth Round against Premier League side Fulham as Kettering twice pulled level before losing 4–2. He was named as the Conference North's Player of the Month for March 2008. He ended the 2008–09 season with eight goals in 45 games, but was released by Kettering in May 2009.

Westcarr started the 2013–14 season well in another game against Tranmere, bagging a brace and creating a goal in a 3–1 home victory over the Merseyside club. He finished the season as the club's top-scorer with 17 goals in 48 appearances. However, he was released by manager Dean Smith in May 2014. Smith later explained his decision of releasing Westcarr as for the best.

He was transfer-listed by new manager Paul Cook in November 2012, along with Neal Trotman. He scored three goals in 18 appearances in the first half of the 2012–13 season before he left the Proact Stadium after his contract was cancelled by mutual agreement in January 2013.

Westcarr joined League One club Walsall on a temporary loan deal in November 2012. He signed a permanent deal with Walsall in January after he was released by Chesterfield. He scored his first goal for the "Saddlers" at the Bescot Stadium in a 3–1 win against nearby Shrewsbury Town on 2 March. He then continued his fine form by scoring a 30-yard thunderbolt against fellow play-off hopefuls Tranmere Rovers 10 days later, which won the club's Goal of the Season award. He signed a new one-year contract in July 2013.

He continued to be a key player for the club under three more different manager – Craig Short, Paul Ince and Martin Allen – in the 2010–11 season, scoring 12 goals in 41 League One games for County. On 8 January 2011, he scored the opening goal past Premier League side Sunderland in an FA Cup giant-killing victory at the Stadium of Light.

Westcarr signed a two-year contract with John Sheridan's Chesterfield in August 2011 after moving for an undisclosed fee (reported as £70,000). He hit 11 goals in 43 appearances for the "Spireties" in the 2011–12 season as the club were relegated out of League One. Despite suffering in the league, the club found success in the Football League Trophy by beating Swindon Town 2–0 at Wembley Stadium; Westcarr replaced Jack Lester after 37 minutes and scored the second goal of the game deep into injury-time.

Westcarr joined Ian McParland's League Two side Notts County in May 2009. Off the pitch the club became unstable, as McParland was replaced by Hans Backe and then Steve Cotterill as an unknown investment company took control of the club. On the pitch Westcarr remained a mainstay as the club won promotion as league champions. He scored 11 goals in 50 games, including a hat-trick against Hereford United in a 5–0 win at Meadow Lane on 27 February. He signed a new two-year deal with the "Magpies" in June 2010.

He was moved out to the wing by manager Mark Cooper for the 2007–08 season, and helped the club to win promotion as divisional champions. In May 2008 Kettering reported Conference Premier side Stevenage Borough to the Football Association and Conference for allegedly making an illegal approach to Westcarr. He featured during pre-season for Stevenage, before he returned to Kettering for the start of the new campaign.

Westcarr signed with Conference North club Kettering Town in May 2006. The "Poppies" finished the 2006–07 campaign in second place, but were denied promotion after losing to Farsley Celtic in the play-off semi-finals.

Westcarr joined Conference National club Cambridge United on a short-term contract in September 2005 after impressing during a trial period. He scored eight goals in 34 matches in the 2005–06 season as Rob Newman's "U's" posted a 12th-place finish. He chose to leave the Abbey Stadium in May 2006 after rejecting the offer of a permanent contract.

He joined League Two club Lincoln City on loan in December 2004. He scored on his debut for Keith Alexander's "Imps" on 1 January, the only goal of the game with Bury at Sincil Bank. He played five further games before returning to Nottingham at the end of the month. He spent April 2005 on loan at Danny Wilson's Milton Keynes Dons, failing to score in four substitute appearances during his time at Stadium mk. He was one of 12 players released by Forest in May 2005 after the club were relegated out of the Championship under Gary Megson.

He played 13 games in the 2002–03 campaign, scoring his first goal in senior football on 4 May, in a 2–2 draw with Rotherham United at Millmoor. However, he made only four appearances in the 2003–04 campaign, and dropped out of the first team picture under new manager Joe Kinnear.

Born in Nottingham, Nottinghamshire, Westcarr played for Nottingham Forest as a youth, and became the youngest player to ever play for the club, aged 16, when he came on for David Johnson 83 minutes into a 1–0 win over Burnley at the City Ground on 13 October 2001. He made a further seven First Division appearances in the 2001–02 under the stewardship of Paul Hart.

Westcarr won caps for the England under-15, under-16, under-17 and under-18s. He played in the 2001 UEFA European Under-16 Championship, where England finished fourth.

Craig Naptali Westcarr (born 29 January 1985) is an English professional footballer who plays as a striker for Grantham Town.