Poplar, London born outside left Les Clenshaw began his football career with Westhill before joining Third Division (South) club Southend United as an amateur in August 1924, turning professional in July 1925. After a spell on loan at Chelmsford during 1925-26, he made his Football League debut at Brentford in September 1926, but had to wait until March 1928 to establish himself as a first team regular. He scored 4 goals in a 5-2 win over Mansfield Town in March 1932 as The Shrimpers finished third in the League that season.
In May 1934 he left Southend after 30 goals in 141 appearances, and joined Barrow, where he scored 8 goals in 33 appearances during his single season at Holker Street. He joined Mansfield Town in September 1935, where he scored 6 goals in 30 appearances before returning to non league Chelmsford in the summer of 1936, subsequently playing for Gaslight of Rayleigh in 1937 before finishing his playing career.