| Winner | Runner-up | |
| 1903 | Sharnford | |
| 1904 | Leire | |
| 1905 | Bitteswell | |
| 1906 | Bitteswell | |
| 1907 | Arnesby | |
| 1908 | Leire | |
| 1909 | Leire | Arnesby |
| 1910 | Leire | |
| 1911 | Arnesby | |
| 1912 | Bitteswell | Kimcote by Walton |
| 1913 | Bitteswell | Dunton Bassett |
| 1914 | Kimcote by Walton | |
| 1915-1918 | No competition | |
| 1919 | Bitteswell | Gilmorton |
| 1920 | Kimcote by Walton | |
| 1921 | Gilmorton | |
| 1922 | Willoughby Waterless | |
| 1923 | Bitteswell | |
| 1924 | Kimcote by Walton | |
| 1925 | Dunton Bassett | Willoughby Waterless |
| 1926 | Kimcote by Walton | Dunton Bassett |
| 1927 | Ashby Magna | Leire |
| 1928 | Gilmorton | Willoughby Waterless |
| 1929 | Bitteswell | Ashby Magna |
| 1930 | Leire | Gilmorton |
| 1931 | Willoughby Waterless | Bitteswell |
| 1932 | Bitteswell | |
| 1933 | Dunton Bassett | |
| 1934 | Arnesby | Leire |
| 1935 | Leire | Ashby Magna |
| 1936 | Willougby Waterless | Leire |
| 1937 | Willougby Waterless | Leire |
| 1938 | Kimcote by Walton | Ashby Magna |
| 1939 | Willoughby Waterless | Dunton Bassett |
Richard Holdridge
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