Donated by the club's founder, and awarded to a member who has made an outstanding contribution during the year. This can be based on outstanding competition results, service to the club or a combination of both. Long term service to the club is a further criterion. Nominations are made by members to the Club Secretary odsec@octavian-droobers.org by 1st December in any year. The trophy is awarded at the Annual Dinner (usually held in February or March).
| 2021 | Margaret Willdig |
| 2020 | Bruce Bryant |
| 2019 | Sheila Carey |
| 2018 | Liz Phillips |
| 2017 | Melanie Elkington |
| 2016 | Sue Hallett |
| 2015 | Andy Emmerson |
| 2014 | John Middler |
| 2013 | Karin Kirk |
| 2012 | Richard Gardner |
| 2011 | Sue Bicknell |
| 2010 | John Bowman |
| 2009 | Carolyn Marr |
| 2008 | Iain Embrey |
| 2007 | Alan Halliday |
| 2006 | Martin Cross |
| 2005 | Peter Guillaume |
| 2004 | Frank Smith |
| 2003 | Greta Shields |
| 2002 | Paul Furness |
| 2001 | Miranda and Ulli |
| 2000 | Steve Bates |
| 1999 | Jane Halliday |
| 1998 | Bruce Bryant |
| 1997 | Bob Brandon |
| 1996 | T & H Simpson |
| 1995 | Tony Haw |
| 1994 | Mike Hampton |
| 1993 | Peter Guillaume |
| 1992 | Barry Elkington |
| 1991 | Maureen Chapman |
| 1990 | N/A |
| 1989 | Terry Foxton |
| 1988 | Bob Carey |
| 1987 | Pip Skinner |