1920s

1929/30 Nethy Bridge FC

1930s

1930/31 Nethy Bridge FC

1932/33 Nethy Bridge FC

1933/34 Boat of Garten FC

1934-37 Not Recorded

1938/39 Boat of Garten FC

1940s

1940-45 No competition – WW2

1946/47 Boat of Garten FC

1947/48 Kingussie FC

1948/49 Aviemore FC

1949/50 Aviemore FC

1950s

1950/51 Aviemore FC

1951/52 Aviemore FC

1952/53 Aviemore FC

1954 Aviemore FC

1955 REM (Royal Engineers)

1956 Nethy Bridge FC

1957 Nethy Bridge FC

1958 Nethy Bridge FC

1959 Kingussie FC

1960s

1960 Kingussie FC

1961 Kingussie FC

1962 Aviemore FC

1963 Aviemore FC

1964 Kingussie FC

1965 Kingussie FC

1966 Aviemore Thistle FC

1967 Kingussie FC

1968 Grantown FC

1969 Grantown FC

1970s

1970 Kingussie FC

1971 Carrbridge FC

1972-73 Not Recorded

1974 Carrbridge FC

1975 Carrbridge FC

1976 Kingussie FC

1977 Aviemore Thistle FC

1978 Carrbridge FC

1979 Carrbridge FC

1980s

1980 Kingussie FC

1981 Carrbridge FC

1982 Grantown FC

1983 Newtonmore FC

1984 Kingussie FC

1985 Grantown FC

1986 Grantown FC

1987 Grantown FC

1988 Aviemore Thistle FC

1989 Grantown FC

1990s

1990 Grantown Utd FC

1991 Grantown Utd FC

1992 Grantown Utd FC

1993 Coylum Bridge FC

1994 Coylum Bridge FC

1995 Kingussie FC

1996 Grantown Utd FC

1997 Aviemore United

1998 Aviemore Utd FC

1999 Grantown Utd FC

2000s

2000 Kingussie FC

2001 Kingussie FC

2002 Kingussie FC

2003 Kingussie FC

2004 Cromdale FC

2005 Tomatin FC

2006 Aviemore Thistle FC

2007 Tomatin FC

2008 Carrbridge FC

2009 RBL Aviemore FC

2010s

2010 Strathspey Thistle Colts FC

2011 Kingussie FC

2012 Kingussie FC

2013 Strathspey Thistle Colts FC

2014 Grantown FC

2015 Grantown Utd FC

2016 Grantown Utd FC

2017 Grantown Utd FC

2018 Grantown FC

2019 Grantown Utd FC

2020s

2020 No Competition – COVID19

2021 No Competition – COVID19

2022 Boat of Garten Ospreys FC

2023 Aviemore Thistle FC