| Year | Winners | Runners Up |
| First Division | | |
| 1929 | Brechin | Meigle |
| 1930 | Brechin | Arbroath United |
| 1931 | Brechin | Blairgowrie |
| 1932 | Brechin | Arbroath United |
| 1933 | Brechin | Arbroath United |
| 1934 | Arbroath United | Brechin |
| 1935 | Arbroath United | Strathmore |
| 1936 | Arbroath United | Strathmore |
| 1937 | Brechin, Mannofield XI | |
| 1938 | Mannofield XI | Brechin |
| 1939 | Not completed | |
| 1940 | Forthill XI | Mannofield XI |
| 1941-1945 | no competition | | |
| 1946 | Strathmore | Perthshire XI |
| 1947 | Strathmore | Gordonians |
| 1948 | Aberdeen GSFP | Perthshire XI |
| 1949 | Mannofield XI,Perthshire XI, Strathmore | |
| 1950 | Strathmore | Meigle |
| 1951 | Perthshire XI | Strathmore |
| 1952 | Strathmore | Perthshire XI |
| 1953 | Perthshire XI | Strathmore |
| 1954 | Meigle | Brechin |
| 1955 | Strathmore | Meigle |
| 1956 | Brechin | Strathmore |
| 1957 | Strathmore | Meigle |
| 1958 | Perthshire XI | Arbroath, Brechin |
| 1959 | Arbroath United | Brechin |
| 1960 | Perthshire XI | Strathmore |
| 1961 | Meigle | Brechin |
| 1962 | Strathmore | Brechin |
| 1963 | Strathmore | Perthshire XI |
| 1964 | Strathmore | Arbroath United |
| 1965 | Blairgowrie | Strathmore |
| 1966 | Strathmore | Forthill XI |
| 1967 | Strathmore | Perthshire XI |
| 1968 | Strathmore | Blairgowrie |
| 1969 | Strathmore | Meigle |
| 1970 | Strathmore | Blairgowrie |
| 1971 | Strathmore | Blairgowrie |
| 1972 | Strathmore | Brechin |
| 1973 | Arbroath United | Brechin |
| 1974 | Brechin | Strathmore |
| 1975 | Brechin | Strathmore |
| 1976 | Strathmore | Brechin |
| 1977 | Brechin | Aberdeen Grammar School Former Pupils |
| 1978 | Arbroath, Dundee High School Former Pupils | |
| 1979 | Arbroath United | Meigle |
| 1980 | Meigle | Strathmore |
| 1981 | Strathmore | Forthill XI |
| 1982 | Aberdeen Grammar School Former Pupils | Dundee High School Former Pupils |
| 1983 | Strathmore | Aberdeen Grammar School Former Pupils |
| 1984 | Arbroath United | Meigle |
| 1985 | Arbroath United | Meigle |
| 1986 | Arbroath United | Brechin |
| 1987 | Aberdeen Grammar School Former Pupils | Arbroath United |
| 1988 | Arbroath United | Dundee High School Former Pupils |
| 1989 | Dundee High School Former Pupils | Aberdeen Grammar School Former Pupils |
| 1990 | Aberdeen Grammar School Former Pupils | Gordonians |
| 1991 | Strathmore | Dundee High School Former Pupils |
| 1992 | Mannofield | Dundee High School Former Pupils |
| 1993 | Dundee High School Former Pupils | Brechin |
| 1994 | Gordonians | Inverurie |
| 1995 | Dundee HSFP | Inverurie |
| 1996 | Stoneywood Dyce | Dundee High School Former Pupils |
| 1997 | Stoneywood Dyce | Dundee High School Former Pupils |
| 1998 | Meigle | Aberdeen Grammar School Former Pupils |
