Year   Regular Season                 Playoff Champions
2008 - Kolberg                           Kolberg
2007 – Kolberg                            Kolberg
2006 – Kolberg                            Maplewood
2005 - West Jacksonport               Maplewood
2004 – Institute                           Maplewood
2003 - West Jacksonport               West Jacksonport
2002 - West Jacksonport               Kolberg
2001 - Washington Island              Washington Island
2000 – Maplewood                       Egg Harbor
1999 – Institute                           Egg Harbor
1998 - West Jacksonport               Baileys Harbor
1997 – Kolberg                            Institute
1996 - West Jacksonport-              Kolberg
1995 – Maplewood                       Kolberg
1994 - Sister Bay                         Institute
1993 - Sister Bay                         Institute
1992 – Maplewood                       Maplewood
1991 - Sister Bay                         Maplewood
1990 - Sister Bay                         Maplewood
1989 - Sister Bay                         Maplewood
1988 - Sister Bay                         Sister Bay
1987 - Egg Harbor                        West Jacksonport
1986 - West Jacksonpor                Sister Bay
1985 - Sister Bay                         Sister Bay
1984 - West Jacksonport               Sister Bay
1983 - Sister Bay                         Sister Bay
1982 - Baileys Harbor                   Maplewood
1981 - Sister Bay                         Sister Bay
1980 - West Jacksonport               Maplewood
1979 – Maplewood                       Egg Harbor
1978 – Maplewood                       Sister Bay
1977 - Sister Bay                         Sister Bay
1976 – Maplewood                       Maplewood
1975 - Sister Bay                         Washington Island
1974 - West Jacksonport               Sister Bay
1973 - West Jacksonport               West Jacksonport
1972 - West Jacksonport               Institute
1971 – Institute                           Washington Island
1970 - West Jacksonport               West Jacksonport
1969 – Institute                           Sister Bay
1968 – Institute                           West Jacksonport
1967 – Kolberg                            Institute
1966 – Kolberg                            Kolberg
1965 - Egg Harbor                        West Jacksonport
1964 – North-West Jacksonport South-Maplewood          West-Jacksonport
1963 – North-West Jacksonport South-Institute              West Jacksonport
1962 - North--Egg Harbor South—Kolberg                      Egg Harbor
1961 - North--West Jacksonport South—Brussels            Brussels
1960 - North--West Jacksonport South--Sturgeon Bay     West Jacksonport
1959 – Brussels                           Brussels
1958 – Brussels                           Brussels
1957 - West Jacksonport               Washington Island
1956 - West Jacksonport               Egg Harbor
1955 - Washington Island              West Jacksonport
1954 - Top Of The Thumb              Washington Island
1953 - Top Of The Thumb              Baileys Harbor
1952 - Little Sturgeon                   Egg Harbor
1951 - Washington Island              Washington Island