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