In 1985 the club organised a charity ride to Gloucester’s twin town of Gouda in response to the visit by Gouda riders the year before. The Club President (Ted Tedaldi) was presented with a Church Warden’s clay pipe made by a master craftsman. He in turn presented it to the Club to be awarded for the best overseas ride, as judged by vote at the AGM. In 2024, the trophy being somewhat the worse for wear, it was retired and returned to Ted Tedaldi. The best overseas tour has since been rewarded with the Prestbury Cancer Centenary Trophy.
| Year | Winner | Location of ride |
|---|---|---|
| 2024 | Malcolm Taylor | Colorado & Utah |
| 2023 | Simon & Theresa Pollington | The Netherlands |
| 2022 | Alastair Goldie | Tuscany |
| 2021 | Not awarded | |
| 2020 | Not awarded | |
| 2019 | Alastair Goldie | Cyprus |
| 2018 | Pete & Sue Lloyd (tandem) | Holland |
| 2017 | Adrian Pearce | Haute Alpes |
| 2016 | Paul Bridges & John Flint | Spain |
| 2015 | Pete Lloyd et al | |
| 2014 | Graham Denny | Menali to Leh |
| 2013 | Graham Denny | |
| 2012 | Martyn & Ann Willliams (tandem) | Holland |
| 2011 | Gary & Julie Ridgeway (tandem) | Holland |
| 2010 | Derek Dowdeswell | Normandy Beaches |
| 2010 | Derek Dowdeswell | |
| 2009 | Ed Spurway | Pyrenees end to end |
| 2008 | Graham Denny | Rwanda |
| 2003 | Dave Lesser & Theo Brookes | |
| 2002 | Alastair Goldie & Matthew Utting | |
| 2001 | Nigel & Debbie Light | |
| 2000 | Theo Brookes | |
| 1998 | Alastair Goldie | |
| 1997 | Alastair Goldie | |
| 1996 | Alastair Goldie | |
| 1995 | Toby Wooldridge | |
| 1994 | Martin Thompson | |
| 1993 | Toby Wooldridge | |
| 1992 | Mike Davies | |
| 1991 | D. & K. Rowlatt | |
| 1990 | A. Robbins | |
| 1989 | R. Langley | |
| 1988 | C. Marley & P.Crocker | |
| 1987 | G. Carter | |
| 1986 | S. Adams |