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.[2]
Whelpdale began his senior career at Maldon Town, after not being offered a scholarship by Ipswich, before moving shortly to Billericay Town.
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.[3] Whelpdale was part of the Gillingham side that won the 2012–13 League Two title.[4]
Stevenage
He rejected a new deal from Gillingham and signed for League Two side Stevenage on 30 June 2014.[5]
On 28 July 2017, Whelpdale re-signed for Stevenage.[8] Whelpdale made 27 League Two appearances, starting 19 times, scoring once, before departing the club.[9]
Chelmsford City
On 10 August 2018, Whelpdale signed for Chelmsford City.[10] On 27 August 2018, Whelpdale scored his first goal for the club in a 5–3 away win against Hemel Hempstead Town.[11] On 30 January 2020, Whelpdale was confirmed as assistant to interim manager Robbie Simpson alongside Michael Spillane following the sacking of Rod Stringer.[12]
On 19 July 2023, Whelpdale signed for Isthmian League Premier Division club Lewes.[14] 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.[15]
Burgess Hill Town
On 19 October 2024, Whelpdale joined Isthmian League South East Division club Burgess Hill Town.[16]
Career statistics
As of match played 15 October 2024
Appearances and goals by club, season and competition