Colts Medal Winners
| Year | Winner | Club |
| 2020 | Sam Hackett | Hunters Hill |
| 2019 | Jack Crombie | Forest |
| 2018 | Ben Rooney | Hunters Hill |
| 2017 | Josh Bones | Epping |
| 2016 | Jack Hardy | Forest |
| 2015 | Max Maddison | UNSW |
| 2014 | Charles Cradock | Hills |
| 2013 | Chris Charlwood | Balmain |
| 2012 | James Curnow | Balmain |
| 2011 | Nick Gillespie | Old Ignatians |
| 2010 | Sam Jenkins | Barker Old Boys |
| 2009 | Will Martin | Colleagues |
| 2008 | Johnathon Broome | Lindfield |
| 2007 | Lachlan Bursle | Roseville |
| 2006 | Steve Quinn | Petersham |
| 2005 | Jordan Thompson | Colleagues |
| 2004 | Steve Goodare | Mosman |
| 2003 | Dan Kelly | Colleagues |
| 2002 | Karl Hamilton | Mosman |
| 2001 | Clayton Moise | Dundas |
| 2000 | William Bye | Dundas |
| 1999 | Peter Minucos | Colleagues |
