Living in Brentwood,
Essex, Chris Whelpdale joined the Norwich City set-up at Colchester
/ Potters Bar run by Roy Massey and Graham Scales, playing for
their Under-11s in 1997/98. He later played for Maldon Town of
the Southern League and was selected for England Schoolboys in
Chris moved to Billericay Town in October 2006 where his form
was spotted by league sides. At the time of writing, it appears
that Peterborough had beaten off interest from Swansea and Millwall,
by offering Chris a four year contract. This was signed in mid-May
2007 despite competition from Southend and Dagenham
Chris scored 7 goals in 2008/9 as Peterborough won promotion
into The Championship from League One
Chris and Peterborough were relegated at the end of the 2009/10
season after a traumatic season that saw the Posh use three different
On 12th November 2010, Charlie was loaned for a month to Gillingham
along with Posh teammate Charlie Lee. Whelpdale has been loaned
to Gills to regain match fitness following an injury. He scored
on his debut the following day in a 3-1 home defeat to Crewe.
Returning to Peterborough, Whelpdale did not make the first team
suqad and was the subject of a bid for a second loan spell with
Gillingham in March 2011. This was blocked by Peterborough with
Chairman Barry Fry saying: We wont be signing anyone
because we believe we have a good enough squad to go up, and because
we want to go up there wont be anyone going out either.
Chris was on the bench when Peterborough beat Lee
Clark's Huddersfield 3-0 in the League One Play-off Final
on 29th May 2011 to secure promotion back to the Premiership
Chris was transferred to Gillingham in July 2011, signing a three
On 30th June 2014, Whelpdale was one of three players signed
by Stevenage (the others being Ronnie Henry and Simon Walton).
Whelpdale had played 108 league games for Gillingham.
On 28th June 2016, Whelpdale signed for League One side AFC Wimbledon following his release from Stevenage. He had scored nine goals in 24 appearances for Boro in 2015/16 from midfield.
On 28th July 2017, Whelpdale returned to Stevenage. He had scored twice in 23 appearances for Wimbledon.