Career
Wakefield started his career in local football in Shanklin, he then moved to Bournemouth and started a two-year apprenticeship in the summer of 2010. In November 2011, Wakefield joined Wimborne Town along with Billy Maybury on a one-month work experience deal. In January 2012, he was again sent out on loan, joining Hamworthy United.
He made his debut for the Hammers in a 4–0 defeat to Moneyfields.
In April 2012, Wakefield was offered his first professional contract, on a one-year deal. On 30 April 2012, he was drafted into first team duty, making his debut in a 1–1 draw with Scunthorpe United, coming on as a substitute for Donal McDermott in the second half.
On 19 August 2015, Wakefield joined League Two side Yeovil Town on a one-month loan deal, and made his debut that evening against York City. On 25 February 2016, Wakefield joined League One side Walsall on loan until the end of the season.