Premiers - Nicholson Cup
| Year | Premiers |
| 2022 | Not Contested |
| 2021 | Not Contested |
| 2020 | Newport |
| 2019 | Newport |
| 2018 | Barker Old Boys |
| 2017 | Redfield Old Boys |
| 2016 | Beecroft |
| 2015 | King's Old Boys |
| 2014 | Briars |
| 2013 | Waverley |
| 2012 | Colleagues Convicts |
| 2011 | Blue Mountains |
| 2010 | Brothers |
| 2009 | Merrylands |
| 2008 | Hunters Hill |
| 2007 | Petersham |
| 2006 | Blue Mountains |
| 2005 | HUnters Hill |
| 2004 | Blue Mountains |
| 2003 | Barker Old Boys |
| 2002 | Liverpool |
| 2001 | Blue Mountains |
| 2000 | Blue Mountains |
| 1999 | Petersham |
| 1998 | Canterbury |
| 1997 | Drummoyne |
| 1996 | Killara West Pymble |
| 1995 | Blue Moutains |
