Perpetual trophies are awarded for various Twenty Hundred Club events. Click on the links to read the requirements for the trophy, and see the historical results.
| Races with Four Classes | Spinnaker A | Spinnaker B | Cruise-I | Cruise-II |
| Around Aquidneck Race | Prudence Trophy | Tequila Trophy | Brenton Trophy | Gibbs Trophy |
| Block Island Race | Street Trophy | Bounty Trophy | Shaw Trophy | John Dickerson Trophy |
| Around Prudence Race | Rives Trophy | Sheldon Trophy | Hope Trophy | Charles Dickerson Trophy |
| Races with Two Classes | Spinnaker | Cruising | ||
| Cuttyhunk Race | Haas Trophy | Cuttyhunk Trophy | ||
| Prince Henry Race | Navigator Trophy | Manickas Trophy | ||
| Special Trophies | ||||
| Dilemma Trophy | Best Around Aquidneck Challenge (spinnaker) | |||
| John Brady Trophy | Best Around Aquidneck Challenge (non-spinnaker) | |||
| Clean Up Trophy | Best Combined Corrected VMG Around Islands (Aquidneck/Prudence) | |||
| Clark Trophy | Best Sportsman | |||
| Windholme Trophies | Best Barrington YC Boat corrected time Cuttyhunk Race | |||
| Phyllis Bowen Trophy | Best 3 races (spinnaker) | |||
| Lynne Charlton Trophy | Best 3 races (non-spinnaker) | |||
| Dawson Trophy | Best 4 races (any class) | |||
| Topaz Trophy | Best East Greenwich YC Boat corrected time Cuttyhunk Race | |||