 On 17 June 2014 Westcarr joined Portsmouth on a free transfer after leaving Walsall, penning a two-year contract.He represented England at under-15, under-16, under-17 and under-18 level.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.