| Year | Club | |
| 2017 | Canterbury | |
| 2016 | Blacktown | |
| 2015 | Beecroft | |
| 2014 | Redfield Old Boys | |
| 2013 | Not Contested | |
| 2012 | Not Contested | |
| 2011 | Brothers | |
| 2010 | Not Contested | |
| 2009 | Not Contested | |
| 2008 | Merrylands | |
| 2007 | UWSH | |
| 2006 | Fairvale Old Boys | |
| 2005 | Oatley | |
| 2004 | Hills | |
| 2003 | Blakehurst | |
| 2002 | Knox Old Boys | |
| 2001 | Liverpool | |
| 2000 | Hurlstone Park | |
| 1999 | Hurlstone Park | |
| 1998 | Matraville | 4th Div CC |
| 1997 | Not Contested | |
| 1996 | Not Contested | |
| 1995 | UNSW | Div 1 CC with Colts |
| 1994 | St Patrick's | Div 1 CC with Colts |
| 1993 | Hornsby | Div 1 CC with Colts |
| Prior to 1993, the Herlihy Shield was awarded in the Metropolitan Rugby | ||
