 Cleared from Collingwood to Essendon A in the VFA in July 1912, Diggle played in 44 First XVIII matches for Essendon from 1912 to 1915, and 3 games in the post-war VFA competition in 1919.From 1920 to 1924, he was captain-coach of the Seymour Football Club in the Waranga North East Football Association.The team won two premierships in Diggle's time as coach