| Year | Winner | Runner-up |
| 3 Counties Cup | ||
| 1935 | Brechin | Meigle |
| 1936 | Blairgowrie | Arbroath |
| 1937 | Arbroath | Strathmore |
| 1938 | Forthill XI | Mannofield XI |
| 1939 | Gordonians | Strathmore |
| 1940 | Forthill XI | Mannofield XI |
| 1941-1946 | no competition | |
| 1947 | Strathmore | Gordonians |
| 1948 | Perthshire XI | Strathmore |
| 1949 | Gordonians | Strathmore |
| 1950 | Gordonians | Meigle |
| 1951 | Meigle | Montrose |
| 1952 | Strathmore | Aberdeen Grammar School Former Pupils |
| 1953 | Gordonians | Forthill XI |
| 1954 | Brechin | Meigle |
| 1955 | Forthill XI | Strathmore |
| 1956 | Brechin | Aberdeen Grades |
| 1957 | Forthill XI | Strathmore |
| 1958 | Aberdeen Grammar School Former Pupils | Strathmore |
| 1959 | Aberdeen Grammar School Former Pupils | Brechin |
| 1960 | Withheld | Strathmore, Aberdeen University |
| 1961 | Mannofield XI | Arbroath |
| 1962 | Brechin | Forthill XI |
| 1963 | Strathmore | Meigle |
| 1964 | Strathmore | Perthshire Cricket Association |
| 1965 | Strathmore | Brechin |
| 1966 | Strathmore | Perthshire Cricket Association |
| 1967 | Aberdeen Grades | Strathmore |
| 1968 | Strathmore | Aberdeen Grades |
| 1969 | Strathmore | Meigle |
| 1970 | Perthshire XI | Strathmore |
| 1971 | Aberdeen Grades | Strathmore |
| 1972 | Blairgowrie | Aberdeen Grades |
| 1973 | Perthshire Cricket Association | Perthshire XI |
| 1974 | Blairgowrie | Arbroath |
| 1975 | Mannofield XI | Blairgowrie |
| 1976 | Dundee High School Former Pupils | Strathmore |
| 1977 | Dundee High School Former Pupils | Aberdeen Grammar School Former Pupils |
| 1978 | Strathmore | Meigle |
| 1979 | Strathmore | Arbroath |
| 1980 | Meigle | Strathmore |
| 1981 | Forthill XI | Perthshire Cricket Association |
| 1982 | Mannofield XI | Perthshire Cricket Association |
| 1983 | Meigle | Strathmore |
| 1984 | Meigle | Arbroath |
| 1985 | Arbroath | Forthill XI |
| 1986 | Arbroath | Dundee High School Former Pupils |
| 1987 | Dundee High School Former Pupils | Arbroath |
| 1988 | Brechin | Dundee High School Former Pupils |
| 1989 | Dundee High School Former Pupils | Brechin |
| 1990 | Aberdeen Grammar School Former Pupils | Perth |
| 1991 | Aberdeen Grades | Dundee High School Former Pupils |
| 1992 | Aberdeen Grades | Brechin |
| 1993 | Dundee High School Former Pupils | Aberdeen Grades |
| 1994 | Inverurie | Brechin |
| 1995 | Aberdeen Grades | Forthill |
| 1996 | Aberdeen Grades | Strathmore |
| 1997 | Dundee High School Former Pupils | Stoneywood Dyce |
| 1998 | Meigle | Strathmore |
| 1999 | Aberdeen Grades | Perth |
| 2000 | Meigle | Stoneywood Dyce |
| 2001 | Perth | Huntly |
| 2002 | Arbroath | Perth |
| 2003 | St Modans | Strathmore |
| 2004 | Huntly | Forthill |
| 2005 | Arbroath | Aberdeen Grades |
| 2006 | Huntly | Perth |
| 2007 | Strathmore | Dundee High School Former Pupils |
| 2008 | Forthill | Aberdeen Grades |
| 2009 | Aberdeen Grades | Forthill |
| 2010 | Aberdeen Grades | Strathearn |
| 2011 | Huntly | Kinloch |
| 2012 | Aberdeen Grades | Perth Doo’Cot |
| 2013 | Aberdeen Grades | Perth Doo’Cot |
| 2014 | Aberdeen Grades | Dundee High School Former Pupils |
| 2015 | Gordonians | Meigle |
| 2016 | Gordonians | Meigle |
| 2017 | Forthill | Mannofield |
| 2018 | Gordonians | Meigle |
| 2019 | Dundee HSFP | Arbroath |
| 2020 | no competition | |
| 2021 | no competition | |
| 2022 | Perth Doo’Cot | Meigle |
| T20 Cup | ||
| 2023 | Perth Doo’Cot | Gordonians |
Alan Veitch, Neil Leitch