Ryan won the 1934 - Albury & District Football League's best and fairest award, the Stavley Medal, playing for the Albury Rovers Football Club, before heading down to Melbourne to play with Fitzroy.[3][4]
Ryan debuted in the VFL in 1935, in round one, aged just 18 and started his career at centre half forward, topping Fitzroy's goalkicking in his debut season with 46 goals. He was moved to centre half back the following season and won the 1936 Brownlow Medal, with 26 votes, making it the fifth Brownlow in the previous six years to have gone to a Fitzroy player.
In 1939 after injuring his knee, Ryan joined the army and fought in World War II, serving for four years.[5] He was wounded as one of the "Rats of Tobruk" and later served 18 months on the front line in New Guinea.[6]
Ryan did appear in a practice match for Fitzroy in March, 1946,[7] but he never played VFL football after the end of World War Two.