Donald Gray Memorial Cup
The Donald Gray Memorial Cup is the premier men's football competition in Southland, New Zealand. It sits below the Southern Football Premier League and above Southland Division 1.
Current clubs
As of 2025 season.| Team | Stadium | Location | 2024 season |
| Gore Wanderers | Hyde Park | Gore | 2nd |
| Old Boys | Waverley Park | Invercargill | 4th |
| Queens Park | Surrey Park | Invercargill | 1st |
| Thistle | ILT Football Turf | Invercargill | 3rd |
| Waihopai | Surrey Park | Invercargill | 5th |
| Winton | Central Southland College | Winton | — |
Past winners
;List of winners from 1950-2009;List of winners from 2003–
- 1950 - Brigadiers
- 1951 - Brigadiers
- 1952 - Brigadiers
- 1953 - Brigadiers & Thistle FC
- 1954 - Brigadiers
- 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 - Southland 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 - Southend United
- 1999 - Queenstown Rovers
- 2000 - Queenstown Rovers
- 2001 - Waihopai
- 2002 - Waihopai
- 2003 - Waihopai
- 2004 - Queens Park AFC
- 2005 - Southend United
- 2006 - Queens Park AFC
- 2007 - Southend United
- 2008 - Queens Park AFC
- 2009 - Old Boys' AFC
- 2010 - Old Boys' AFC
- 2011 - Old Boys' AFC
- 2012 - Old Boys' AFC
- 2013 - Southend United
- 2014 - Old Boys' AFC
- 2015 - Queenstown Rovers
- 2016 - Old Boys' 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