The County Medals competition for Oakham was only formed in the 1934/35 season. Before that the teams from Rutland competed in the Melton County Medals.

	Winners	Runners Up
1934/35	Burley	Langham
1935/36	Oakham Rovers	Greetham United
1936/37	Oakham Rovers	Burley
1937/38	North Luffenham	Langham
1938/39	Greetham United	Langham
1939/40	Cottesmore RAF	Burley

The competition was suspended due to war between 1940 and 1946.

After the war ended the regional County Medals competitions format was changed to be a larger county wide format with the formation of the County Medals East & West in 1946.