Men’s First Grade Premiers
| YEAR | WINNER | YEAR | WINNER | YEAR | WINNER |
| 2020 | Terrigal United FC | 2001 | Ourimbah United FC | 1982 | Umina United SC |
| 2019 | Killarney District SC | 2000 | Umina United SC | 1981 | Umina United SC |
| 2018 | Killarney District SC | 1999 | Wyong SC | 1980 | Wyong SC |
| 2017 | Killarney District SC | 1998 | Ourimbah United FC | 1979 | Wyoming FC |
| 2016 | Killarney District SC | 1997 | Southern & Ettalong FC | 1978 | Wyoming FC |
| 2015 | The Entrance FC | 1996 | Gosford City FC | 1977 | Wyong FC |
| 2014 | The Entrance FC | 1995 | Gosford City FC | 1976 | Wyoming FC |
| 2013 | Wyoming FC | 1994 | Wyong SC | 1975 | Wyoming FC |
| 2012 | Wyoming FC | 1993 | Wyong SC | 1974 | Southern United |
| 2011 | Umina United SC | 1992 | Southern & Ettalong FC | 1973 | Southern United |
| 2010 | The Entrance FC | 1991 | Southern & Ettalong FC | 1972 | Budgewoi FC |
| 2009 | Wyoming FC | 1990 | Wyong SC | 1971 | Woy Woy FC |
| 2008 | Umina United SC | 1989 | The Entrance FC | 1970 | Budgewoi FC |
| 2007 | Wyoming FC | 1988 | Umina United FC | 1969 | Ettalong Beach |
| 2006 | Umina United SC | 1987 | East Gosford FC | 1968 | The Entrance FC |
| 2005 | The Entrance FC | 1986 | Umina United SC | 1967 | Narara Wyoming |
| 2004 | Wyoming FC | 1985 | Wyong SC | 1966 | Brisbania |
| 2003 | Killarney District SC | 1984 | Umina United SC | |
| 2002 | East Gosford FC | 1983 | Wyong SC | |
