Chudleigh was signed as an amateur at the start of the 1936/37 season, he had been playing for Ladybirds F.C.

A forward, (who usually played at outside-left) who made his debut against Folkestone on the 19th of September 1936, for Exeter City reserves, Two days later he scored his first goal for the reserves, against Bideford in a friendly.

He continued to play for the Southern league and Devon & Exeter League teams