After playing local football in
Brentwood, Whelpdale was recruited by
Norwich City's youth academy. Whelpdale later moved to
Arsenal and
Ipswich Town before being released. Whelpdale began his senior career at
Maldon Town, after not being offered a scholarship by Ipswich, before moving shortly to
Billericay Town.
Peterborough United In 2007 Whelpdale signed for
League Two side
Peterborough United, rejecting
League One side
Southend United, who had just been relegated from the
Football League Championship.
Gillingham He joined
Gillingham on loan in the 2010–11 season and scored three goals in four games for the
League Two team. He joined Gillingham on a permanent basis in July 2011. Whelpdale was part of the Gillingham side that won the 2012–13 League Two title.
Stevenage He rejected a new deal from Gillingham and signed for
League Two side
Stevenage on 30 June 2014.
AFC Wimbledon On 28 June 2016 Whelpdale signed for
League One side
AFC Wimbledon. He scored his first goal for Wimbledon in a 3–2
EFL Cup loss against
Peterborough United on 9 August 2016. Whelpdale made 27 League Two appearances, starting 19 times, scoring once, before departing the club.
Chelmsford City On 10 August 2018, Whelpdale signed for
Chelmsford City. On 27 August 2018, Whelpdale scored his first goal for the club in a 5–3 away win against
Hemel Hempstead Town. On 30 January 2020, Whelpdale was confirmed as assistant to interim manager
Robbie Simpson alongside
Michael Spillane following the sacking of Rod Stringer.
Eastbourne Borough On 29 July 2020, Whelpdale left Chelmsford to join fellow
National League South club
Eastbourne Borough.
Lewes On 19 July 2023, Whelpdale signed for
Isthmian League Premier Division club
Lewes. He scored on his league debut against
Cray Wanderers on 12 August.
Whitehawk On 17 June 2024, Whelpdale joined fellow Isthmian Premier Division side
Whitehawk.
Burgess Hill Town On 19 October 2024, Whelpdale joined Isthmian League South East Division club
Burgess Hill Town. == Career statistics ==