Plympton, Devon born inside forward Harry Raymond played as a youth for Crownhill Juniors, Crownhill reserves and Woodland Stars. In 1905 he signed for Crownhill before a spell with Woodland Villa in 1907, from whom he joined Southern League club Plymouth Argyle in 1908, making his debut at Bristol Rovers that September, scoring his first goal for Argyle in a 2-2 draw with Brighton & Hove Albion in October 1909. Raymond retained his amateur status well into his Argyle career but gradually forced his way into the first team and became one of the club’s most consistent performers over the next seven years, playing at both inside forward positions.
The Argyle handbook describes Raymond as “one of the most brilliant forwards this district has produced” and “a perfect artist with the ball, but most unselfish”. His talent soon attracted wider attention: he was selected as one of 15 non-travelling reserves for the GB side at the 1912 Stockholm Olympics and earned three amateur caps for England between November 1913 and February 1914, scoring on his England debut in a 2-0 win over Ireland at The Oval, Belfast and in a 9-1 victory over Wales at Home Park in his final cap, as well as being chosen for The Southern League representative side.
The First World War interrupted his career, during which he played for Motherwell as a guest, but he returned to Argyle after the cessation of hostilities. Raymond played five more seasons for the club, assisting in the transition to the Football League, playing 30 times in their inaugural 1920-21 League campaign, before leaving Home Park after 16 years and 50 goals in 257 appearances to finish his career with a stint as player-manager of Torquay United in 1924.