A product of local football, Len Wheeler was playing for Bournemouth in the Hampshire County League when he had a trial match for the Saints, in December 1912, in a Southern Charity Cup match. He continued to play for Bournemouth but then signed Southampton, on Southern League forms, in September 1913.

More than a year later, he played his one game at that level – his second and last peace-time match, at centre-forward, for the Saints. He was, however, prominent in the first season of war-time matches, forming the nucleus of the attack with Arthur Dominy and Joe Blake. His 27 goals in 31 games, friendlies included, was an impressive return for that 1915-16 season, which he followed up with six in nine in 1916-17, before he joined the Royal Garrison Artillery as a Bombardier. After the War, he returned to play as an amateur for Bournemouth, while working as a travelling representative in the coal trade.