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 January 2005.

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 managers.

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 won’t be signing anyone because we believe we have a good enough squad to go up, and because we want to go up there won’t 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 year deal.