Regatta Winners
LYRA 2000
| Trophy | Awarded For | Boat | Skipper | Boat Type | Home Club |
| Ashbridge’s Bay YC Trophy | Harrier | Chris Chapman | Tartan 30 | National Yacht Club | |
| Baldwin Trophy | Dynamo | Eric Moog | Farr 40 | Royal Canadian Yacht Club | |
| Bamann Trophy | NOBODY’S BUSINESS | ||||
| Bud Doyle Trophy | BRAIN CRAMP | ||||
| Charles Freeman Cup | Dynamo | Eric Moog | Farr 40 | Royal Canadian Yacht Club | |
| City of Hamilton Mayor’s Cup | The Fish | Jay Tovey | J/29 | Rochester Yacht Club | |
| City of Toronto Mayor’s Trophy | NOBODY’S BUSINESS | ||||
| Commodore Gooderham Trophy | Norseman | Ced Gyles | 8 Metre | Royal Canadian Yacht Club | |
| Commodore World Cup | POLESTAR | ||||
| Douglas B. Jones Trophy | Blue Knight | Peter Pape | J/35 | Rochester Yacht Club | |
| Golden Eagle Trophy | Dynamo | Eric Moog | Farr 40 | Royal Canadian Yacht Club | |
| Hinterholler Trophy | Hot Tamale | Christopher Clarke | Gilbert 25 | National Yacht Club | |
| Hispaniola Trophy | Das Blau Max | Cliff Sertl | J/35 | Rochester Yacht Club | |
| John T. Mott Trophy | Natural | John Fowler | 8 Metre | Sodus Bay Yacht Club | |
| Johnstone Trophy | PLAY TIME | ||||
| Kay Heron Trophy | Das Blau Max | Cliff Sertl | J/35 | Rochester Yacht Club | |
| Lake Ontario Trophy | Dynamo | Eric Moog | Farr 40 | Royal Canadian Yacht Club | |
| Louise Freeman Cup | Das Blau Max | Cliff Sertl | J/35 | Rochester Yacht Club | |
| LYRA Boat of the Year | HARRIER, R. Porter | ||||
| LYRA Founders Cup | NOBODY’S BUSINESS | ||||
| LYRA President’s Trophy | Moongator | Peter Quackenbush | J/33 | Sodus Bay Yacht Club | |
| National Yacht Club Trophy | Harrier | Chris Chapman | Tartan 30 | National Yacht Club | |
| Olcott Cup | Natural | John Fowler | 8 Metre | Sodus Bay Yacht Club | |
| Oswego Founders Cup | Blue Knight | Peter Pape | J/35 | Rochester Yacht Club | |
| PHRF-LO President’s Cup | The Fish | ||||
| Queen City Yacht Club Trophy | Natural | John Fowler | 8 Metre | Sodus Bay Yacht Club | |
| RYC Centennial Cup | Das Blau Max | Cliff Sertl | J/35 | Rochester Yacht Club | |
| Tom Taylor Trophy | SURVIVAL | ||||
| W.P. Montgomery Trophy | LIGHTNING | ||||
| Yacht Racing Union Cup | Dynamo | Eric Moog | Farr 40 | Royal Canadian Yacht Club |
| Trophy | Winner For | Awarded |
| Blake Van Winkle Trophy | Helen Ingerson, RYC |