He was born in Plymouth, where he began his career with amateur team Woodland Villa.
[1] He joined Southern League club Plymouth Argyle in 1908, but chose to retain his status as an amateur for a number of years.
[2] He made his debut in a 1–0 win at Bristol Rovers in September 1908 and scored his first goal for Argyle in a 2–2 draw with Brighton & Hove Albion in October 1909.
[3] Raymond won the Southern League championship with the club in 1913 and earned three amateur caps for England before competitive football was suspended for the duration of the First World War.
[3] He left in 1924, having scored 50 goals in 257 appearances, to finish his career with Southern League side Torquay United as player-manager.