| Cup name | Helm first name | Helm surname | Club | Crew name | Boat Number | Boatname | Venue | Year | Notes | |
|---|---|---|---|---|---|---|---|---|---|---|
| Weston Bay Yacht Club Tro | Paul | Winterflood | GSC | 535 | Ozone Frlendly | Torbay | 2013 | |||
| Anonymous (Leaky Boat) | Tim | Parkinson | TSC | Diana Parkinson | 565 | Avocet | Fishguard | 2012 | ||
| Monday | Tim | Parkinson | TSC | Diana Parkinson | 565 | Avocet | GSC | 2012 | ||
| Poole Y.C. Trophy | Murray | Glenister | PYC | 659 | Lyberty | 2012 | ||||
| Smartie Plate | Adam | Gray | GSC | James Davies | 673 | Icarus | Fishguard | 2012 | ||
| Weston Bay Yacht Club Tro | Paul | Winterflood | GSC | 535 | Ozone Frlendly | Fishguard | 2012 | |||
| Anonymous (Leaky Boat) | Tim | Parkinson | TSC | Diana Parkinson | 565 | Avocet | Weymouth | 2011 | ||
| Monday | Richard | Twyman | GSC | Debbie Twyman | 612 | Hazy Daze | GSC | 2011 | ||
| Poole Y.C. Trophy | Murray | Glenister | PYC | 659 | Lyberty | 2011 | ||||
| Seamanship | Tim | Parkinson | TSC | Diana Parkinson | 565 | Avocet | Weymouth | 2011 | Sailed back with oar as rudder in race 4. Finished race 5 with jibstick as tille More ... | |
| Smartie Plate | Emma | Griffen | PYC | Weymouth | 2011 | |||||
| Weston Bay Yacht Club Tro | John | Lokier | PYC | Phil Lokier | 632 | Don't Panic | Weymouth | 2011 | First winner | |
| Anonymous (Leaky Boat) | Tim | Parkinson | TSC | Diana Parkinson | 565 | Avocet | Salcombe | 2010 | ||
| Graham Penny Trophy | Tim | Parkinson | TSC | Diana Parkinson | 565 | Avocet | 2010 | |||
| Monday | Chris | Steer | GSC | 610 | Crystal Dawn | GSC | 2010 | |||
| Poole Y.C. Trophy | Peter | Hewitt | PYC | 649 | Mandarin | 2010 | ||||
| Smartie Plate | Emma | Griffen | PYC | Salcombe | 2010 | |||||
| Anonymous (Leaky Boat) | Tim | Parkinson | TSC | Diana Parkinson | 565 | Avocet | Fishguard | 2009 | ||
| Graham Penny Trophy | Tim | Parkinson | TSC | Diana Parkinson | 565 | Avocet | 2009 | |||
| Ladies Race Trophy | Diana | Parkinson | Tim Parkinson | 565 | Avocet | 2009 | ||||