Senior Men’s Flags winners
| Year | Winner | Runner-up | Score |
|---|---|---|---|
| 1883–1884 | South Manchester | Heaton Mersey | 8–5 |
| 1884–1885 | Liverpool | Heaton Mersey | 9–3 |
| 1885–1886 | South Manchester | Liverpool | 5–3 |
| 1886–1887 | Owens College | Liverpool | 3–2 |
| 1887–1888 | Owens College | South Manchester | 6–5 |
| 1888–1889 | South Manchester | Owens College | 3–1 |
| 1889–1890 | South Manchester | Heaton Mersey | 15–5 |
| 1890–1891 | South Manchester | Owens College | 4–1 |
| 1891–1892 | South Manchester | Owens College | 6–2 |
| 1892–1893 | Cheetham | South Manchester | 6–2 |
| 1893–1894 | Cheetham | Owens College | 4–3 |
| 1894–1895 | South Manchester | Owens College | 10–3 |
| 1895–1896 | Stockport | South Manchester | 9–5 |
| 1896–1897 | Stockport | Albert Park | 2–1 |
| 1897–1898 | Stockport | South Manchester | 9–3 |
| 1898–1899 | Stockport | Heaton Mersey | 16–2 |
| 1899–1900 | Stockport | Albert Park | 12–0 |
| 1900–1901 | Stockport | Heaton Mersey | 11–3 |
| 1901–1902 | Stockport | South Manchester | 6–1 |
| 1902–1903 | Stockport | South Manchester | 12–5 |
| 1903–1904 | South Manchester | Heaton Mersey | 9–4 |
| 1904–1905 | Stockport | Heaton Mersey | 9–4 |
| 1905–1906 | South Manchester | Stockport | 3–2 |
| 1906–1907 | Old Hulmeians | South Manchester | 10–7 |
| 1907–1908 | Old Hulmeians | South Manchester | 10–7 |
| 1908–1909 | South Manchester | Eccles | 11–4 |
| 1909–1910 | Old Hulmeians | South Manchester | 10–4 |
| 1910–1911 | Stockport | Old Hulmeians | 6–1 |
| 1911–1912 | Stockport | Albert Park | 7–3 |
| 1912–1913 | Stockport | Albert Park | 11–2 |
| 1913–1914 | Old Hulmeians | Heaton Mersey | 10–6 |
| 1915–1918 | No Contest | No Contest | |
| 1919–1920 | South Manchester | Albert Park | 6–5 |
| 1920–1921 | Boardman | South Manchester | 12–4 |
| 1921–1922 | Boardman | Old Hulmeians | 11–5 |
| 1922–1923 | Old Hulmeians | Stockport | 6–4 |
| 1923–1924 | South Manchester | Stockport | 7–4 |
| 1924–1925 | Albert Park | Stockport | 8–3 |
| 1925–1926 | Stockport | Heaton Mersey Guild | 15–5 |
| 1926–1927 | Heaton Mersey | Old Mancunians | 12–6 |
| 1927–1928 | Stockport | Heaton Mersey Guild[1] | 16–1 |
| 1928–1929 | Boardman | Eccles | 9–1 |
| 1929–1930 | Old Mancunians | Stockport | 4–3 |
| 1930–1931 | Stockport | Old Mancunians | 5–4 |
| 1931–1932 | Old Hulmeians | Heaton Mersey | 7–3 |
| 1932–1933 | South Manchester & Wythenshawe | Stockport | 10–3 |
| 1933–1934 | Stockport | Old Mancunians | 7–6 |
| 1934–1935 | Mellor | Old Mancunians | 9–4 |
| 1935–1936 | Mellor | Old Hulmeians | 13–5 |
| 1936–1937 | Mellor | Old Waconians | 9–5 |
| 1937–1938 | Old Waconians | Old Hulmeians | 8–6 |
| 1938–1939 | Old Waconians | Boardman & Eccles | 7–2 |
| 1940–1945 | No Contest | No Contest |
| 1946–1947 | Old Waconians | Old Hulmeians | 9–2 |
| 1947–1948 | Mellor | Boardman & Eccles | 5–4 |
| 1948–1949 | Old Hulmeians | Ashton | 10–7 |
| 1949–1950 | Old Hulmeians | Mellor | 9–7 |
| 1950–1951 | Old Waconians | Old Mancunians | 9–8 |
| 1951–1952 | Old Waconians | Old Mancunians | 7–4 |
| 1952–1953 | Old Waconians | Old Hulmeians | 8–4 |
| 1953–1954 | Heaton Mersey | Old Hulmeians | 8–7 |
| 1954–1955 | Old Waconians | Old Hulmeians | 10–5 |
| 1955–1956 | Old Hulmeians | Old Mancunians | 8–5 |
| 1956–1957 | Old Mancunians | Heaton Mersey | 9–7 |
| 1957–1958 | Heaton Mersey | Old Mancunians | 5–4 |
| 1958–1959 | Heaton Mersey | Old Hulmeians | 4–1 |
| 1959–1960 | Heaton Mersey | Manchester University | 8–6 |
| 1960–1961 | Boardman & Eccles | Manchester University | 8–6 |
| 1961–1962 | Old Hulmeians | South Manchester & Wythenshawe | 6–1 |
| 1962–1963 | Mellor | Heaton Mersey | 15–7 |
| 1963–1964 | Old Hulmeians | Heaton Mersey | 10–3 |
| 1964–1965 | Mellor | Old Hulmeians | 7–5 |
| 1965–1966 | South Manchester & Wythenshawe | Old Hulmeians | 11–5 |
| 1966–1967 | Mellor | South Manchester & Wythenshawe | 12–11 |
| 1967–1968 | Old Hulmeians | Mellor | 6–5 |
| 1968–1969 | Mellor | Cheadle | 19–4 |
| 1969–1970 | South Manchester & Wythenshawe | Mellor | 9–5 |
| 1970–1971 | South Manchester & Wythenshawe | Urmston | 18–5 |
| 1971–1972 | South Manchester & Wythenshawe | Urmston | 7–5 |
| 1972–1973 | South Manchester & Wythenshawe | Mellor | 11–2 |
| 1973–1974 | Urmston | Sheffield University | 12–5 |
| 1974–1975 | Urmston | Sheffield University | 14–7 |
| 1975–1976 | Old Hulmeians | South Manchester & Wythenshawe | 12–8 |
| 1976–1977 | Sheffield University | Urmston | 17–11 |
| 1977–1978 | Cheadle | South Manchester & Wythenshawe | 10–4 |
| 1978–1979 | Cheadle | Mellor | 15–11 |
| 1979–1980 | South Manchester & Wythenshawe | Old Hulmeians | 14–10 |
| 1980–1981 | Cheadle | Mellor | 13–7 |
| 1981–1982 | Sheffield University | Cheadle | 13–11 |
| 1982–1983 | Sheffield University | Cheadle | 15–10 |
| 1983–1984 | Cheadle | South Manchester & Wythenshawe | 15–8 |
| 1984–1985 | Cheadle | Old Hulmeians | 12–5 |
| 1985–1986 | Heaton Mersey | Stockport | 10–8 |
| 1986–1987 | Stockport | Mellor | 9–8 |
| 1987–1988 | Mellor | Stockport | 11–6 |
| 1988–1989 | Stockport | Cheadle | 9–8 |
| 1989–1990 | Cheadle | Mellor | 7–6 |
| 1990–1991 | Cheadle | Stockport | 10–9 |
| 1991–1992 | Cheadle | Heaton Mersey | 15–12 |
| 1992–1993 | Heaton Mersey | Timperley | 13–9 |
| 1993–1994 | Cheadle | Mellor | 11–8 |
| 1994–1995 | Cheadle | Mellor | 9–4 |
| 1995–1996 | Stockport | Mellor | 7–4 |
| 1996–1997 | Mellor | Heaton Mersey | 13–10 |
| 1997–1998 | Cheadle | Heaton Mersey | 8–7 |
| 1998–1999 | Stockport | Heaton Mersey | 13–6 |
| 1999–2000 | Cheadle | Heaton Mersey | 14–7 |
| 2000–2001 | Cheadle | Old Waconians | 9–7 |
| 2001–2002 | Heaton Mersey | Stockport | 14–13 |
| 2002–2003 | Cheadle | Mellor | 15–13 |
| 2003–2004 | Stockport | Heaton Mersey | 14–13 |
| 2004–2005 | Stockport | Heaton Mersey | 14–10 |
| 2005–2006 | Heaton Mersey | Stockport | 6–4 |
| 2006–2007 | Manchester Waconians | Mellor | 9–3 |
| 2007–2008 | Wilmslow | Mellor | 19–10 |
| 2008–2009 | Cheadle | Stockport | 9–8 |
| 2009–2010 | Stockport | Rochdale | 9–2 |
| 2010–2011 | Cheadle | Heaton Mersey | 9–8 |
| 2011–2012 | Stockport | Cheadle | 15–2 |
| 2012–2013 | Stockport | Cheadle | 8–6 |
| 2013–2014 | Cheadle | Stockport | 10–8 |
| 2014–2015 | Cheadle | Heaton Mersey | 14–8 |
| 2015–2016 | Poynton | Cheadle | 8–7 |
| 2016–2017 | Poynton | Cheadle | 14–8 |
| 2017–2018 | Poynton | Cheadle | 10–6 |
| 2018–2019 | Poynton | Cheadle | 13–11 (OT) |
| 2019–2020 | No Contest | No Contest | |
| 2020–2021 | No Contest | No Contest | |
| 2021–2022 | Heaton Mersey | Stockport | 14–11 |
| 2022–2023 | Cheadle | Brooklands Hulmeians | 10–6 |