| 4/4/20 |
District 8 Laser Regatta |
| 4/18/20 |
Oyster Bay Challenge |
| 5/6-9/30/20 |
Wednesday Night Fleet Racing at Sagamore YC |
| 5/9/20 |
Alfred Roosevelt Regatta |
| 5/23-5/24/20 |
Outlaw Trophy |
| 5/24/20 |
Cayenne Trophy Series (1 of 3) |
| 5/30-5/31/20 |
Women's Invitational |
| 6/13/20 |
Squaw Cup |
| 6/20-6/21/20 |
Commodore Swan Cup |
| 6/26-8/14/20 |
Summer Solstice Series |
| 6/28/20 |
Cayenne Trophy Series (2 of 3) |
| 7/4/20 |
Junior-Senior Challenge |
| 7/11-7/12/20 |
Annual Rendezvous |
| 7/15/20 |
Kiwassa Cup |
| 7/15-7/19/20 |
Commodores' International Cup |
| 7/18-7/26/20 |
Eastern Cruise |
| 7/25-7/26/20 |
Corinthian Young Guns |
| 8/1/20 |
Dooley Roosevelt Regatta |
| 9/2-9/5/20 |
Thompson Cup |
| 9/5/20 |
Stratford Shoal Race |
| 9/6/20 |
Fall Regatta (One-Designs) |
| 9/7/20 |
Fall Regatta (PHRF) |
| 9/12/20 |
Elihu Root Trophy |
| 9/16/20 |
Benzie Cup |
| 10/3-10/4/20 |
Middle Sound Race |
| 10/4/20 |
Cayenne Trophy Series (3 of 3) |
| 10/10-10/12/20 |
Lee Family Trophy |
| 10/17-10/18/20 |
Invitational Cruise Cup |