| Winner | Runner-up | |
| 1927 | Glossop | Swinton |
| 1928 | Longsight | Unsworth |
| 1929 | Glossop | Levenshulme |
| 1930 | Longsight | Unsworth |
| 1931 | Unsworth | Glossop |
| 1932 | Unsworth | Stand |
| 1933 | Prestwich | Cheetham |
| 1934 | Longsight | Stand |
| 1935 | Stand | Denton St Lawrence |
| 1936 | Denton St Lawrence | Longsight |
| 1937 | Stalybridge | Macclesfield |
| 1938 | Macclesfield | Stalybridge |
| 1939 | East Levenshulme | |
| Macclesfield | ||
| 1940-1945 | No competition – Second World War | |
| 1946* | Dukinfield | Swinton |
| 1947* | Longsight | Dukinfield |
| 1948* | Stalybridge | Bollington |
| 1949* | Stand | Unsworth |
| 1950* | Longsight | Levenshulme |
| 1951 | Longsight | Macclesfield |
| 1952 | Stalybridge | Levenshulme |
| 1953 | Macclesfield | Stalybridge |
| 1954 | Macclesfield | Levenshulme |
| 1955 | Macclesfield | Bollington |
| 1956 | Glossop | Denton St Lawrence |
| 1957 | Glossop | Unsworth |
| 1958 | Denton St Lawrence | Stalybridge |
| 1959 | Denton St Lawrence | Denton |
| 1960 | Longsight | Marple |
| 1961** | Glossop | Stand |
| 1962** | Stand | Longsight |
| 1963 | Denton St Lawrence | Marple |
| 1964 | Bollington | Prestwich |
| 1965 | Longsight | Stalybridge |
| 1966 | Glossop | Longsight |
| 1967 | Dukinfield | Stalybridge |
| 1968 | Unsworth | Stalybridge |
| 1969 | Longsight | Bollington |
| 1970 | Longsight | Norden |
| 1971 | Stalybridge | Dukinfield |
| 1972 | Denton St Lawrence | Unsworth |
| 1973 | Stalybridge | Longsight |
| 1974 | Denton St Lawrence | Greenmount |
| 1975 | Denton West | Glossop |
| 1976 | Denton | Romiley |
| 1977 | Unsworth | Longsight |
| 1978 | Hyde | Denton St Lawrence |
| 1979 | Poynton | Stalybridge |
| 1980 | Stalybridge | Woodbank |
| 1981 | Greenmount | Moorside |
| 1982 | Unsworth | Glossop |
| 1983 | Unsworth | Stalybridge |
| 1984 | Unsworth | Denton St Lawrence |
| 1985 | Newton Heath | Longsight |
| 1986 | Denton | Thornham |
| 1987 | Longsight | Unsworth |
| 1988 | Longsight | Denton St Lawrence |
| 1989 | Longsight | Denton St Lawrence |
| 1990 | Woodhouses | Denton |
| 1991 | Darcy Lever | Glossop |
| 1992 | Darcy Lever | Glossop |
| 1993 | Denton | Woodhouses |
* – Awarded as an aggregate trophy
** – Awarded to First XI scoring highest number of points from 14th game to end of season
Richard Isaacs
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