Wagstaff joined Charlton Athletic at the age of 8 after being spotted at a Charlton Athletic Community course. . He then captained Charlton's Under 18s on their run to the FA Youth Cup quarter finals. He made his debut in April 2008 against Barnsley, in the same match as Jonjo Shelvey made his debut.[1] In the same season he was named as the club's young player of the year.[2] Wagstaff joined Bournemouth on a month's loan in August 2008 and to Northwich Victoria for a month in November 2008.[3] In December 2008 he was given a 2+1⁄2-year professional contract by Charlton manager Alan Pardew.[4]
Wagstaff scored his first goal for Charlton in a league game against Walsall on 22 August 2009.[5]
He was released by Charlton at the end of the 2012–13 season.[6]
Bristol City
On 8 July 2013, Wagstaff signed for Bristol City on a three-year deal.[7] He made his debut for Bristol City in a 2–2 draw against Bradford City, and scored in that game.[8]
On 27 June 2016 Bristol City confirmed that Wagstaff would be leaving the club in search of first-team football.[9]
Gillingham
He joined League One side Gillingham on a two-year deal on 7 July 2016.[10] He scored his first goal for Gillingham in a 3–3 draw with Chesterfield on 27 September 2016.[11]
He was released by Gillingham at the end of the 2017–18 season.[12]
AFC Wimbledon
On 11 July 2018 it was announced the Wagstaff had signed with League One side AFC Wimbledon.[13] On 26 January, Wagstaff scored two goals in AFC Wimbledon's FA Cup 4th Round defeat of West Ham United at Kingsmeadow.[14]
Wagstaff was released by the club at the conclusion of the 2019–20 season,[15] having made 72 appearances in all competitions and scoring 6 goals.[16]