Regatta Winners
Canceled due to COVID-19
| Trophy | Awarded For | Boat | Skipper | Boat Type | Home Club |
| Ashbridge’s Bay Yacht Club Trophy | Give‘r | Tim Sweet | J/88 | National Yacht Club | |
| Bud Doyle Bowl | Shakedown | John Enwright | Olcott Yacht Club | ||
| Centennial Canada Cup | Sarissa | Ralph Reimann | 8 Metre Modern | Etobicoke Yacht Club | |
| Centennial Canada Cup | Sarissa | Bert Reimann | 8 metre | Etobicoke Yacht Club | |
| Charles Freeman Cup | Afterburn | Darren Gornall | Soto 40 | Port Credit Yacht Club | |
| Commodore Gooderham Trophy | Bangalore | 8mR Classic | Royal Canadian Yacht Club | ||
| Commodore World Cup | TriMe | Dan Klick | Contour 34 | Bronte Harbour Yacht Club | |
| Fredric Nichols Trophy | Wind Chill | Mark Schimley | Beneteau First 36.7 | Youngstown Yacht Club | |
| John Labatt Trophy | Wild Thing Tamed | Edward Thompson | Oakville Club | ||
| John T. Mott Trophy | Wind Chill | Mark Schimley | Beneteau First 36.7 | Youngstown Yacht Club | |
| Johnstone Trophy | Hijinks | Laura Weyler | Olcott Yacht Club | ||
| Kay Heron Trophy | Tiburon | Dirk Knueulman | Etchells | Oakville Yacht Club | |
| Lake Ontario PHRF Bowl | Wild Thing Tamed | Edward Thompson | Oakville Club | ||
| Louise Freeman Cup | Shakedown | John Enwright | Olcott Yacht Club | ||
| LYRA Boat of the Year - Handicap | Give‘r | Tim Sweet | J/88 | National Yacht Club | |
| LYRA PHRF Cup | Zone | Ken Bruce | Beneteau First 40.7 | Port Credit Yacht Club | |
| National Yacht Club Trophy | Boom | Scott Lyons | Olson 30 | Oakville Yacht Club | |
| Oswego Founder’s Cup | Founders Race | Shakedown | John Enwright | Olcott Yacht Club | |
| PHRF-LO President’s Cup | Elusive | Pierre Boileau | C&C 29-2 | Oakville Yacht Club | |
| Queen City Yacht Club Trophy | Give‘r | Tim Sweet | J/88 | National Yacht Club | |
| Shotgun Trophy | Sarissa | Ralph Reimann | 8 Metre Modern | Etobicoke Yacht Club | |
| Sir Thomas Lipton Cup | Gypsy | Cliff Walkington | R Class | Ashbridges Bay Yacht Club | |
| Sodus Bay Cup | Hijinks | Laura Weyler | Olcott Yacht Club | ||
| Tom Taylor Trophy | Katbird | Kathleen Timmis | Dufour 34 | Royal Canadian Yacht Club | |
| W.P. Montgomery Trophy | Tiburon | Dirk Knueulman | Etchells | Oakville Yacht Club | |
| Whitby Founders Trophy | Wild Thing Tamed | Edward Thompson | Oakville Club | ||
| Yacht Racing Union Cup | Afterburn | Darren Gornall | Soto 40 | Port Credit Yacht Club |
