The Prestbury Cancer Centenary Trophy was given to the club in 1991 for Criterium racing and was subsequently presented to the best placed club rider in the Cotswold Cycle Racing League series. After several years of it going unclaimed, and the League having folded, it was reassigned to the best overseas tour, replacing the Gouda Trophy that was retired in 2024 and is awarded for the best Overseas touring ride by a Club member in the financial year just finished. At the General Committee meeting in September of each year, the General Committee shall nominate worthy Club members. All Club members are to be notified of the Committee’s choice and may vote at the AGM for the candidate they consider should be awarded the Trophy.
| Year | Winner | Venue |
|---|---|---|
| 2024 | Malcolm Taylor | Tour of the Moon (USA) |
| 2023 | Not claimed | Trophy reassigned |
| 2022 | Not claimed | Points earned |
| 2021 | Not claimed | |
| 2020 | Not claimed | |
| 2019 | James Fawbert | 24 |
| 2018 | Dan Kelly | 24 |
| 2017 | Justin Di Tommaso | |
| 2016 | Not awarded | |
| 2015 | Anthony Lake | |
| 2014 | Sean Townsend | 258 |
| 2013 | Lee Finch | 379 |
| 2012 | Adam Beddall | |
| 2011 | Adam Beddall | |
| 2010 | Matt Godden | 18 |
| 2009 | M Watkins | 14 |
| 2008 | Mike Horsman | 2 |
| 2007 | Mike Horsman | 10 |
| 2003 | Ian Humble | |
| 2000 | Not awarded | |
| 1998 | Jason Streather | |
| 1997 | Andy Jarvis | |
| 1996 | Andy Jarvis | |
| 1995 | Not awarded | |
| 1994 | Richard Clements | |
| 1993 | Not awarded | |
| 1992 | Not awarded | |
| 1991 | Nick Yarworth | |
| 1990 | C. Hanby |