September Challenge Cup
For Firefly DinghiesPresented by G F Revill esq.
| Year | 1st | 2nd | 3rd |
| 1949 | J Preston | ||
| 1950 | Edward Austin | ||
| 1951 | J Preston | ||
| 1952 | Les Holmberg | ||
| 1953 | Les Holmberg | ||
| 1954 | Peter Beardsall | ||
| 1955 | Les Holmberg | ||
| 1956 | Edward Austin | ||
| 1957 | Edward Austin | ||
| 1958 | Mike Beardsall | ||
| 1959 | Les Holmberg | ||
| 1960 | Les Holmberg | ||
| 1961 | Les Holmberg | ||
| 1962 | Les Holmberg | ||
| 1963 | Les Holmberg | ||
| 1964 | R Thacker | ||
| 1965 | Les Holmberg | ||
| 1966 | Les Holmberg | ||
| 1967 | D Bull | ||
| 1968 | Les Holmberg | ||
| 1969 | Ken Boorman | ||
| 1970 | Les Holmberg | ||
| 1971 | Les Holmberg | ||
| 1990 | Keith Newnham | ||
| 1991 | Erling Holmberg | ||
| 1992 | Erling Holmberg | ||
| 1999 | Erling Holmberg | ||
| 2000 | Erling Holmberg | ||
| 2001 | Erling Holmberg | ||
| 2002 | Erling Holmberg | ||
| 2003 | Keith Newnham | ||
| 2004 | Keith Newnham | ||
| 2005 | Erling Holmberg | ||
| 2006 | Erling Holmberg | Paul Tanner | Stuart Pierce |
| 2007 | Geoff Howlett (Sean Strevens) |
Erling Holmberg | |
| 2008 | Keith Newnham | Simon Giles | Bob Baker |
| 2010 | Keith Newnham | Erling Holmberg | Paul Grattage |
| 2011 | Erling Holmberg | Keith Newnham | Liam Thom |
| 2012 | Liam Thom | Keith Newnham | Paul Grattage |
| 2013 | Sean McKenna (Brigitte McKenna) |
Keith Newnham | Erling Holmberg |
| 2014 | Sean McKenna (Sophia McKenna) |
Liam Thom | Erling Holmberg |
| 2015 | Simon Giles | Liam Thom | Sean McKenna |
| 2016 | Paul Grattage | Erling Holmberg | Stuart Pierce |
| 2017 | Sean McKenna | Liam Thom | Yvonne Pike |
| 2018 | Mark Pritchard | Liam Thom | |
| 2019 | Sean McKenna | Liam Thom | Stuart Pierce |
| 2020 | Liam Thom | Sean McKenna | Paul Grattage |
| 2021 | Liam Thom | Tony Murrant | Ian Wilkinson |
| 2022 | Ian Wilkinson | Liam Thom | Mark Pritchard |
| 2023 | Kevin Ellis | Stuart Pierce | Yvonne Pike |
| 2024 | Stuart Pierce | Simon Giles | Keith Newnham |
| 2025 | Simon Giles | Liam Thom | Mark Pritchard |
