The winner shall be the club with the highest amassed total number of competition points gained in the Junior Leagues.
| YEAR | WINNER | YEAR | WINNER | YEAR | WINNER |
| 2020 | East Gosford FC | 2001 | Killarney District SC | 1982 | Wyoming FC |
| 2019 | Avoca FC | 2000 | Killarney District SC | 1981 | Wyoming FC |
| 2018 | Terrigal United FC | 1999 | Killarney District SC | 1980 | Wyoming FC |
| 2017 | East Gosford FC | 1998 | Killarney District SC | 1979 | Wyoming FC |
| 2016 | Kanwal Warnervale FC | 1997 | Killarney District SC | 1978 | East Gosford FC |
| 2015 | Kanwal Warnervale FC | 1996 | Killarney District SC | 1977 | East Gosford FC |
| 2014 | Killarney District SC | 1995 | Killarney District SC | 1976 | East Gosford FC |
| 2013 | Killarney District SC | 1994 | Killarney District SC | 1975 | East Gosford FC |
| 2012 | Terrigal United FC | 1993 | Killarney District SC | 1974 | East Gosford FC |
| 2011 | Terrigal United FC | 1992 | Gosford City FC | 1973 | East Gosford FC |
| 2010 | Killarney District SC | 1991 | Killarney District SC | 1972 | East Gosford FC |
| 2009 | Terrigal United FC | 1990 | Wyoming FC | 1971 | East Gosford FC |
| 2008 | Terrigal United FC | 1989 | Wyoming FC | 1970 | East Gosford FC |
| 2007 | Terrigal United FC | 1988 | Wyoming FC | 1969 | East Gosford FC |
| 2006 | Terrigal United FC | 1987 | Wyoming FC | 1968 | East Gosford FC |
| 2005 | Killarney District SC | 1986 | Wyoming FC | 1967 | East Gosford FC |
| 2004 | Killarney District SC | 1985 | Wyoming FC | 1966 | Ettalong Beach |
| 2003 | Killarney District SC | 1984 | Wyoming FC | 1965 | Ettalong Beach |
| 2002 | Killarney District SC | 1983 | Wyoming FC | 1964 | Ettalong Beach |