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| October / 2019 | ||||
| 10/Oct-13/Oct | - | Harvest Moon Regatta | Seabrook, TX, USA | |
| 11/Oct-13/Oct | - | China Coast Race Week | Hong Kong, China | |
| 11/Oct-13/Oct | - | Finnish J 70 Sailing League | Maarianhamina, Finland | |
| 11/Oct-13/Oct | - | XIII Copa de Espana J 80 | Coruna, Spain | |
| 12/Oct-13/Oct | - | Intercollegiate Offshore Regatta | Larchmont, NY, USA | |
| 16/Oct | - | Hong Kong to Vietnam Race | Hong Kong, China | |
| 16/Oct-20/Oct | - | Hong Kong to Vietnam Race 2019 | Hong Kong, SAR, PRC | |
| 17/Oct-19/Sep | - | German J 70 Sailing League | Glucksburg, Germany | |
| 17/Oct-20/Oct | - | J 88 North American Championship | Larchmont, NY, USA | |
| 18/Oct-20/Oct | - | International J 105 Masters Regatta | San Diego, CA, USA | |
| 19/Oct-26/Oct | - | J 24 World Championship | Miami, FL, USA | |
| 19/Oct-26/Oct | - | J 24 World Championship | Miami, FL, USA | |
| 19/Oct | - | Rolex Middle Sea Race | Cowes, Isle of Wight, UK | |
| 19/Oct | - | Rolex Middle Sea Race | , Malta | |
| 19/Oct | - | The Red Bra Regatta | San Francisco, CA, USA | |
| 20/Oct-21/Oct | - | German J 70 Sailing League | Glucksburg, Germany | |
| 20/Oct-25/Oct | - | Helly Hansen NOOD Regatta - Caribbean Championship | Middletown, RI, British Virgin Islands | |
| 20/Oct-20/Oct | - | Oakcliff October Grade 5 | Oyster Bay, NY, USA | |
| 20/Oct | - | Veleziana | Venezia, VE, Italy | |
| 25/Oct-27/Oct | - | J 24 East Coast Championship | Annapolis, MD, USA | |
| 25/Oct-27/Oct | - | J Fest Southwest | Lakewood, TX, USA | |
| 25/Oct-27/Oct | - | Lipton Cup Regatta | San Diego, CA, USA | |
| 26/Oct-14/Nov | - | 20th Anniversary NARC Rally | Newport , RI, USA | |
| 26/Oct-27/Oct | - | Great Pumpkin Regatta | Point Richmond, CA, USA | |
| 26/Oct-27/Oct | - | Oakcliff Halloween Invitational Grade 3 | Oyster Bay, NY, USA | |
| 26/Oct | - | Witches Brew Race | Charleston, SC, USA | |
| 27/Oct-28/Oct | - | J 22 Cooling Down Regatta | Braassemermeer, Netherlands | |
| 27/Oct-28/Oct | - | J 22 Cooling Down Regatta | Braassemermeer, The Netherlands | |
| November / 2019 | ||||
| 01/Nov-04/Nov | - | French J 80 National Championship | La Rochelle, France | |
| 01/Nov-03/Nov | - | WOWZR! (Women on Water - Zonie Regatta | Phoenix, AZ, US | |
| 09/Nov | - | Hot Rum Series I | San Diego, CA, USA | |
| 09/Nov-09/Nov | - | J 22 Vaterchen Frost Regatta | Hamburg, Germany | |