The Lutterworth County Medals competition was introduced in 1920/21, a lot later than other regions and it probably coincided with the formation of the Lutterworth & District Football League.

	Winners	Runners Up
1920/21	Lutterworth Town	Swinford
1921/22	Swinford	Bitteswell
1922/23	Bitteswell	Swinford
1923/24	Bitteswell	Walcote
1924/25	Gilmorton	Willoughby Waterleys
1925/26	Gilmorton	Lutterworth Town Reserves
1926/27	South Kilworth	Gilmorton

The medals competition did not run for three years which coincided with the Lutterworth and District League ceasing to run for those years. It started again when the League reformed for the 1930/31 season.

	Winners	Runners Up
1930/31	Swinford	Gilmorton
1931/32	Swinford	Lutterworth Vedonis
1932/33	Walcote	Pailton
1933/34	Walcote	Gilmorton
1934/35	Lutterworth Town	Gilmorton
1935/36	Dunton Bassett United	Walcote
1936/37	no competition
1937/38	Lutterworth Corinthians	Dunton Bassett United
1938/39	Claybrooke Rovers	Dunton Bassett United
1939/40	abandoned

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.