It all started in 1981. The Glenmaggie Cup was donated by J.J.B. Constructions, Traralgon.
Cup Winners:
| 2019/20 | The Wasp – Darren Penington (GDBC) |
| 2018/19 | Addicted – Michael Johnson (GDBC) |
| 2017/18 | GBR – Greg Banks (NSW) |
| 2016/2017 | HBR Desperado – Liam Holland (VSBC) |
| 2015/2016 | Event cancelled – Inclement weather – Raining |
| 2014 | GP1 – Grant Harrison |
| 2013 | GP1 – Grant Harrison |
| 2012 | GP 1 – Grant Harrison |
| 2011/12 | Budlight Racing – Paul Eade |
| 2010/11 | GP1 – Grant Harrison |
| 2009/10 | KT11 – Daryl Hamilton |
| 2008 | Martini Racing – Guy Hanson |
| 2006/2007 | Not held – no water – Drought |
| 2005 | Warlord – Paul Burton |
| 2004 | Warlord – Paul Burton |
| 2003 | Big Chief – Paul Burton & crew |
| 2001 | Stinga – Peter Lee |
| 1999 | Special Edition – Mick Krusic |
| 1997 | Rival – John Bakker |
| 1996 | Psycho – Paul McNally, A & M Beale |
| 1995 | Rival – S Ferguson, J Bakker |
| 1994 | The Howling – Paul McNally |
| 1993 | The Howling- Paul McNally |
| 1992 | Nova – Peter Scherell, Kevin Miller |
| 1989 | Juz Krusin – Mark Krusic |
| 1988 | Adrenalin – Colin Moss |
| 1987 | Devious – David Graham, Bob Graham |
| 1986 | K1 Drummond Steel – Allan Drummond |
| 1985 | Nova – K Miller, P Scherell |
| 1984 | Psycho – Alan Beale |
| 1983 | Amadash – Archie Robertson |
| 1982 | Amadash – Archie Robertson |
| 1981 | Lucifer – Allan Drummond |