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.

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.

He was released by Stevenage on 8th May 2018. He had made 32 appearances in 2017/18 scoring once.

He then spent time with Chelmsford City in National League South before spending three seasons with Eastbourne Borough. In July 2023 he signed for Lewes who play in the Pitching In Isthmian League. He moved on to Whitehawk in June 2024. In October 2024 he moved on again joining Burgess Hill Town.