Knight Sports Medal - Winners
| Season | Longmuir Shield | Votes | Club | Woolnough Shield | Votes | Club |
| | | | | | |
| 1988/1999 | Marty Lyons | | Brighton C of C | | | |
| 1989/1990 | Con Gorozidis | | Brighton Union | | | |
| 1990/1991 | Con Gorozidis | | Brighton Union | | | |
| M. Cordwell | Brighton Union |
| 1991/1992 | Craig Hitchcock | | Elwood | | | |
| 1992/1993 | Graeme Bell | | East Sandringham | | | |
| 1993/1994 | D. Millar | | Bentleigh ANA | | | |
| 1994/1995 | Steve May | | Moorabbin West | | | |
| 1995/1996 | Chris Gorrie | | Washington Park | | | |
| 1996/1997 | Simon Hede | | Hampton Central | | | |
| 1997/1998 | Brendan Smith | | Le Page Park | | | |
| 1998/1999 | Ben Logan | | Washington Park | | | |
| 1999/2000 | Steve May | | Moorabbin West | | | |
| Yasas Tilekaratne | Brighton Central |
| 2000/2001 | Damian Krotofil | | Mackie | | | |
| 2001/2002 | Paul O’Meara | | Le Page Park | | | |
| 2002/2003 | Craig Amoore | | Hampton Central | | | |
| George Gorozidis | Brighton Union |
| 2003/2004 | Con Gorozidis | | Brighton Union | | | |
| 2004/2005 | Steve May | | Moorabbin West | | | |
| 2005/2006 | Mark Snelling | | Bentleigh ANA | | | |
| 2006/2007 | Stacey Brown | | West Bentleigh | | | |
| 2007/2008 | Con Pothitos | 12 votes | Brighton Union | | | |
| 2008/2009 | Con Pothitos | | Brighton Union | | | |
| Gareth Finney | Washington Park |
| 2009/2010 | Marshall Bunting | 15 votes | Elwood | | | |
| 2010/2011 | Marshall Bunting | 17 votes | Elwood | | | |
| 2011/2012 | Robbie DeHaan | 16 votes | Elwood | | | |
| 2012/2013 | Brad Dolman | 15 votes | Bentleigh ANA | | | |
| 2013/2014 | Ash Russell | 16 votes | Bentleigh Uniting | | | |
| 2014/2015 | Adam Howard | 19 votes | Elwood | | | |
| 2015/2016 | Waqas Hussain | 15 votes | Mackie | | | |
| 2016/2017 | Dale Tormey | 17 votes | CHAG | Stuart Gara Stuart Bell | 13 votes | Brighton Union |
| 2017/2018 | Tim Scott | 14 votes | Bentleigh ANA | Stuart Gara | 11 votes | Brighton Union |
| 2018/2019 | Nick Huttley | 14 votes | West Bentleigh | Leigh Dawkins | 15 votes | Omega |
| 2019/2020 | Jeremy Warner | 15 votes | East Sandringham | Chris Williamson | 16 votes | Washington Park |
| 2020/2021 | Malin Silva | 18 votes | Bentleigh Uniting | Chris Williamson | 17 votes | Washington Park |