| 1911/12 | Mount Pleasant |
| 1912/13 | Mount Pleasant |
| 1913/14 | Kangaroobie |
| 1914/15 | Mount Pleasant |
| 1915/16-1916/17 | No competiion due to the Great War |
| 1917/18 | School of Arts |
| 1918/19 | Mount Pleasant |
| 1919/20 | March |
| 1920/21 | Mount Pleasant |
| 1921/22 | Mount Pleasant |
| 1922/23 | Mount Pleasant |
| 1923/24 | Railway |
| 1924/25 | Mount Pleasant |
| 1925/26 | East Orabge |
| 1926/27 | Mount Pleaseant |
| 1927/28 | Mental Hospital |
| 1928/29 | Mount Pleaseant |
| 1929/30 | Pinnacle Road |
| Mount Pleasant | |
| 1930/31 | Mount Pleasant |
| 1931/32 | Nashdale |
| 1932/33 | Molong |
| 1933/34 | Nashdale |
| 1934/35 | Nashdale |
| 1935/36 | Mental Hospital |
| 1936/37 | Molong |
| 1937/38 | Nashdale |
| 1938/39 | Nashdale |
| 1939/40 | Railway |
| 1940/41 | Railway |
| 1941/42 | Railway |
| 1942/43 | Nashdale |
| 1943/44 | Railway |
| 1944/45 | Railway |
| 1945/46 | Railway |
| 1946/47 | Railway |
| 1947/48 | Blayney |
| 1948/49 | Blayney |
| 1949/50 | Railway |
| 1950/51 | Railway |
| 1951/52 | Mental Hospital |
| 1952/53 | Railway |
| 1953/54 | Nashdale |
| 1954/55 | Railway |
| 1955/56 | Railway |
| 1956/57 | Blayney |
| 1957/58 | Railway |
| 1958/59 | Railway |
| 1959/60 | Railway |
| Rovers | |
| 1960/61 | Blayney |
| 1961/62 | CYMS |
| 1962/63 | Blayney |
| 1963/64 | CYMS |
| 1964/65 | CYMS |
| 1965/66 | CYMS |
| 1966/67 | Millthorpe |
| 1967/68 | Methodists |
| Rovers | |
| 1968/69 | Orange City |
| 1969/70 | Blayney |
| 1970/71 | Orange City |
| 1971/72 | Orange City |
| 1972/73 | Orange City |
| 1973/74 | Orange City |
| 1974/75 | Orange City |
| 1975/76 | Centrals |
| 1976/77 | Centrals |
| 1977/78 | Orange City |
| 1978/79 | Orange City |
| 1979/80 | Centrals |
| 1980/81 | Bloomfield |
| 1981/82 | Orange City |
| 1982/83 | Centrals |
| 1983/84 | CYMS |
| 1984/85 | Waratahs |
| 1985/86 | Waratahs |
| 1986/87 | Waratahs |
| 1987/88 | Centrals |
| 1988/89 | Cavaliers |
| 1989/90 | Cavaliers |
| 1990/91 | Orange City |
| 1991/92 | Cavaliers |
| 1992/93 | Orange City |
| 1993/94 | Centennials |
| 1994/95 | Centennials |
| 1995/96 | St Patricks |
| 1996/97 | ORC |
| 1997/98 | ORC |
| 1998/99 | Orange City |
| 1999/00 | ORC |
| 2000/01 | Cavaliers |
| 2001/02 | Centennials |
| 2002/03 | Cavaliers |
| 2003/04 | Cavaliers |
| 2004/05 | Cavaliers |
| 2005/06 | Cavaliers |
| 2006/07 | Cavaliers |
| 2007/08 | Cavaliers |
| 2008/09 | Cavaliers |
| 2009/10 | Cavaliers |
| 2010/11 | Centrals |
| 2011/12 | Centrals |
| 2012/13 | Orange City |
| 2013/14 | Cavaliers |
| 2014/15 | CYMS |
| 2015/16 | CYMS |
| 2016/17 | Cavaliers |
| 2017/18 | Orange City |
| 2018/19 | Orange City |
| 2019/20 | Orange City |
| 2020/21 | Orange City |
| 2021/22 | St Patricks Old Boys |
| 2022/23 | Cavaliers |
Marque Dubrow