A Grade Pennant Winners
| Year | Year | Club | Year | Club | |
| 1933 | Richmond | 1963 | Richmond | 1993 | Dunheved |
| 1934 | Campbelltown | 1964 | Campbelltown | 1994 | Wallacia |
| 1935 | Liverpool | 1965 | Wallacia | 1995 | Kellyville |
| 1936 | Campbelltown | 1966 | Penrith | 1996 | NP |
| 1937 | Campbelltown | 1967 | Dunheved | 1997 | NP |
| 1938 | Liverpool | 1968 | Camden | 1998 | Leonay |
| 1939 | Camden | 1969 | Camden | 1999 | Dunheved |
| 1940 | NP | 1970 | Penrith | 2000 | NP |
| 1941 | NP | 1971 | Dunheved | 2001 | NP |
| 1942 | NP | 1972 | Penrith | 2002 | Leonay |
| 1943 | NP | 1973 | Windsor | 2003 | Wallacia |
| 1944 | NP | 1974 | Windsor | 2004 | Leonay |
| 1945 | NP | 1975 | Windsor | 2005 | Leonay |
| 1946 | NP | 1976 | Leonay | 2006 | Camden |
| 1947 | Cumberland | 1977 | Leonay | 2007 | Camden |
| 1948 | Liverpool | 1978 | Richmond | 2008 | Camden |
| 1949 | NP | 1979 | Richmond | 2009 | |
| 1950 | Campbelltown | 1980 | Leonay | ||
| 1951 | Richmond | 1981 | Penrith | ||
| 1952 | Dunheved | 1982 | Richmond | ||
| 1953 | Campbelltown | 1983 | Leonay | ||
| 1954 | Campbelltown | 1984 | Penrith | ||
| 1955 | Campbelltown | 1985 | Leonay | ||
| 1956 | Campbelltown | 1986 | Windsor | ||
| 1957 | Campbelltown | 1987 | Wallacia | ||
| 1958 | Camden | 1988 | Antill Park | ||
| 1959 | Camden | 1989 | Leonay | ||
| 1960 | Camden | 1990 | Leonay | ||
| 1961 | Wallacia | 1991 | Dunheved | ||
| 1962 | Camden | 1992 | Leonay |
|
Clubs Wins as at 2008 Leonay 12 Campbelltown10 Camden 10 Richmond 6 Dunheved 5 Wallacia 5 Penrith 4 Windsor 4 Liverpool 3 Antill Park 1 Cumberland 1 Kellyville 1 |
|
