| Date | Player |
| 1999 | Mike Moore |
| 2000 | Pat Devine |
| 2001 | Pat Devine |
| 2002 | Richard Gilbert |
| 2003 | Danny Evans |
| 2004 | Danny Evans |
| 2005 | Peter Childs |
| 2006 | Jeff Scarlett |
| 2007 | Danny Evans |
| 2008 | Terry Peniket |
| 2009 | Danny Evans |
| 2010 | Terry Peniket |
| 2011 | Jeff Scarlett |
| 2012 | Jeff Scarlett |
| 2013 | Jeff Scarlett |
| 2014 | Danny Evans |
| 2015 | Danny Evans |
| 2016 | Andy Walters |
| 2017 | Todd Littlehales |
| 2018 | Marc Scarlett |
| 2019 | Joint Jeff Scarlett + Kevin Scarlett |
| 2020 | Todd Littlehales |
| 2021 | Jeff Scarlett (Belton Woods) |
| 2022 | Andy Walters (Wychwood) |
| 2023 | Roger Blick (Ardencote) |
| 2024 | Jeff Scarlett (Ardencote) |
| 2025 | Richard Gilbert (Cotswold Country Club) |
Fairfield Golf SocietyGolfus Maximus