| ||||
|
| ||||
| September / 2020 | ||||
| 25/Sep-27/Sep | - | J 22 Lake George Open | Lake George, NY, USA | |
| 25/Sep-27/Sep | - | J 24 USA National Championship | Burlington, VT, USA | |
| 25/Sep-03/Oct | - | ORC/ IRC World Championship - CANCELLED | Newport, RI, USA | |
| 26/Sep | - | Alice Cup Race | Charleston, SC, USA | |
| 26/Sep-04/Oct | - | AYC Fall Regatta | Rye, NY, USA | |
| 26/Sep | - | Fall Race to Solomons | Annapolis, MD, USA | |
| 26/Sep-26/Sep | - | Joe Logan | San Francisco, CA, USA | |
| 26/Sep-05/Oct | - | Les Voiles de Saint-Tropez | Saint Tropez, France | |
| 26/Sep-27/Sep | - | Pantaenius J 80 Cup | Rungsted, Denmark | |
| 26/Sep | - | Sail for Hope | Newport, RI, USA | |
| 28/Sep-01/Oct | - | Ibiza Regatta | Sant Antony de Portmany, Baleares, Spain | |
| 28/Sep-03/Oct | - | J 80 World Championship | Newport, RI, USA | |
| 29/Sep-02/Oct | - | 2020 Americas Formula 18 and U.S. Multihull Championships | San Diego, CA, USA | |
| October / 2020 | ||||
| 02/Oct-04/Oct | - | Dutch J 70 Sailing League | Muiden, Netherlands | |
| 02/Oct-02/Oct | - | Italian J 70 Sailing League- Under 21 Championship | Trieste, Italy | |
| 02/Oct-04/Oct | - | Swiss J 70 Super League Finals | Neuenburg, Switzerland | |
| 03/Oct-04/Oct | - | 2020 Porsche of New Orleans Leukemia Cup Regatta | New Orleans, LA, USA | |
| 03/Oct-04/Oct | - | AYC Double Handed Distance Race | Annapolis, MD, USA | |
| 03/Oct-04/Oct | - | AYC Fall Series - Weekend 1 - Small One Design | Annapolis, MD, USA | |
| 03/Oct-04/Oct | - | Italian J 24 National Series IV | Mandello del Lario (LC), Italy | |
| 08/Oct-10/Oct | - | German J 70 Sailing League | Hamburg (Alster), Germany | |
| 09/Oct-11/Oct | - | China Coast Race Week | Hong Kong, China | |
| 09/Oct-11/Oct | - | Finnish J 70 Sailing League | Maarianhamina, Finland | |
| 09/Oct-11/Oct | - | Intercollegiate Offshore Regatta | Larchmont, NY, USA | |
| 10/Oct | - | AYC Fall Series - Weekend 2 - River Course | Annapolis, MD, USA | |
| 10/Oct-11/Oct | - | J Fest Southwest | Lakewood, TX, USA | |
| 14/Oct | - | Hong Kong to Vietnam Race | Hong Kong, China | |
| 15/Oct-18/Oct | - | International J 105 Masters Regatta | San Diego, CA, USA | |
| 17/Oct-18/Oct | - | AYC Fall Series - Weekend 3 - Big One Design & ORC | Annapolis, MD, USA | |
| 17/Oct-17/Oct | - | German J 70 Sailing League | Hamburg (Alster), Germany | |
| 17/Oct-17/Oct | - | Jessica Cup | San Francisco, CA, USA | |
| 17/Oct | - | Rolex Middle Sea Race | Gzira, Malta | |
| 17/Oct | - | The Red Bra Regatta | San Francisco, CA, USA | |
| 18/Oct-19/Oct | - | Italian J 24 National Series V | Cervia, Italy | |
| 18/Oct-18/Oct | - | Oakcliff Sailing October Grade 5 | Oyster Bay, NY, USA | |
| 22/Oct-25/Oct | - | Lipton Cup Regatta | San Diego, CA, USA | |
| 23/Oct-25/Oct | - | Great Pumpkin Regatta | Point Richmond, CA, USA | |
| 23/Oct-25/Oct | - | Italian J 70 Sailing League | Trieste, Italy | |
| 23/Oct-25/Oct | - | J 24 East Coast Championship | Annapolis, MD, USA | |
| 24/Oct-25/Oct | - | Fall Dinghy | San Francisco, CA, USA | |
| 24/Oct-25/Oct | - | Fall Etchells / Lippincott Memorial | Annapolis, MD, USA | |
| 24/Oct | - | Witches Brew Race | Charleston, SC, USA | |
| 25/Oct | - | Harvest Moon Regatta- Bacardi Cup | Seabrook, TX, USA | |
| 25/Oct-28/Oct | - | J 22 Cooling Down Regatta | Braassemermeer, The Netherlands | |
| 29/Oct-01/Nov | - | J 105 North American Championship | Annapolis, MD, USA | |
| 29/Oct-01/Nov | - | J 111 North American Championship | Annapolis, MD, USA | |
| 31/Oct-01/Nov | - | Oakcliff Sailing Halloween Invitational | Oyster Bay, NY, USA | |