| La Donald Gray Memorial Cup è un campionato di calcio neozelandese organizzato dalla Southern Football per le squadre della regione del Southland. |
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| 1950 | BRIGADIERS | |
|---|---|---|
| 1951 | BRIGADIERS | |
| 1952 | BRIGADIERS | |
| 1953 | BRIGADIERS | |
| 1954 | BRIGADIERS | |
| THISTLE FC | ||
| 1955 | THISTLE FC | |
| 1956 | BRIGADIERS | |
| 1957 | HOTSPURS | |
| 1958 | BRIGADIERS | |
| 1959 | INVERCARGILL ROVERS | |
| 1960 | THISTLE FC | |
| 1961 | THISTLE FC | |
| 1962 | THISTLE FC | |
| 1963 | THISTLE FC | |
| 1964 | THISTLE FC | |
| 1965 | THISTLE FC | |
| 1966 | THISTLE FC | |
| 1967 | INVERCARGILL UNITED | |
| 1968 | INVERCARGILL UNITED | |
| 1969 | THISTLE FC | |
| 1970 | THISTLE FC | |
| 1971 | THISTLE FC | |
| 1972 | THISTLE FC | |
| INVERCARGILL UNITED | ||
| 1973 | THISTLE FC | |
| 1974 | SOUTHLAND BOYS' HIGH SCHOOL | |
| 1975 | SOUTHLAND BOYS' HIGH SCHOOL | |
| 1976 | THISTLE FC | |
| 1977 | THISTLE FC | |
| 1978 | QUEENS PARK AFC | |
| 1979 | OLD BOYS' AFC | |
| 1980 | INVERCARGILL UNITED | |
| 1981 | INVERCARGILL UNITED | |
| 1982 | THISTLE FC | |
| 1983 | GORE WANDERERS | |
| 1984 | THISTLE FC | |
| 1985 | OLD BOYS' AFC | |
| 1986 | WAIHOPAI | |
| 1987 | SOUNTHLAND MARIST | |
| 1988 | OLD BOYS' AFC | |
| 1989 | QUEENS PARK AFC | |
| 1990 | THISTLE FC | |
| 1991 | INVERCARGILL UNITED | |
| 1992 | QUEENS PARK AFC | |
| 1993 | THISTLE FC | |
| 1994 | QUEENSTOWN ROVERS | |
| 1995 | QUEENSTOWN ROVERS | |
| 1996 | QUEENSTOWN ROVERS | |
| 1997 | INVERCARGILL UNITED | |
| 1998 | SOUTHLAND UNITED | |
| 1999 | QUEENSTOWN ROVERS | |
| 2000 | QUEENSTOWN ROVERS | |
| 2001 | WAIHOPAI | |
| 2002 | WAIHOPAI | |
| 2003 | WAIHOPAI | |
| 2004 | QUEENS PARK AFC | |
| 2005 | SOUTHLAND UNITED | |
| 2006 | QUEENS PARK AFC | |
| 2007 | SOUTHLAND UNITED | |
| 2008 | QUEENS PARK AFC | |
| 2009 | OLD BOYS' AFC | |
| 2010 | OLD BOYS' AFC | |
| 2011 | OLD BOYS' AFC | |
| 2012 | OLD BOYS' AFC | |
| 2013 | SOUTHLAND UNITED | |
| 2014 | OLD BOYS' AFC | |
| 2015 | QUEENSTOWN ROVERS | |
| 2016 | OLD BPYS' AFC | |
| 2017 | GORE WANDERERS | |
| 2018 | GORE WANDERERS | |
| 2019 | OLD BOYS' AFC | |
| 2020 | QUEENS PARK AFC | |
| 2021 | QUEENS PARK AFC | |
| 2022 | THISTLE FC | |
| 2023 | OLD BOYS' AFC | |
| 2024 | QUEENS PARK AFC | |
| 2025 | WINTON FC |