↓
- 1929/30 Nethy Bridge FC
- 1930/31 Nethy Bridge FC
- 1932/33 Nethy Bridge FC
- 1933/34 Boat of Garten FC
- 1934-37 No competition
- 1938/39 Boat of Garten FC
- 1940-45 No competition
- 1946/47 Boat of Garten FC
- 1947/48 Kingussie FC
- 1948/49 Aviemore FC
- 1949/50 Aviemore FC
- 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
- 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
- 1970 Kingussie FC
- 1971 Carrbridge FC
- 1972-76 No competition
- 1977 Carrbridge FC
- 1978 Carrbridge FC
- 1979 Carrbridge FC
- 1980 Carrbridge FC
- 1981 Kingussie FC
- 1982 Grantown FC
- 1983 Newtonmore FC
- 1984 Coylum Bridge FC
- 1985 Grantown FC
- 1986 Grantown FC
- 1987-89 No competition
- 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 No competition
- 1999 Grantown Utd FC
- 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
- 2010 Strathspey Thistle Colts FC
- 2011 Kingussie FC
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