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| May / 2009 | |||
| 16/May-20/Sep | SAFRAM M2 Speed Tour 2009 (More...) | , Suisse, Switzerland | |
| June / 2009 | |||
| 26/Jun-28/Jun | Acura presents Ullman Sails Long Beach Race Week (More...) | Long Beach , CA, USA | |
| 26/Jun-28/Jun | Grand Prix M2 de Morges / Championnat du Léman (More...) | Morges, Vaud, Switzerland | |
| 26/Jun-01/Jul | Lake Erie Interclub Cruise (More...) | Erie, PA, USA | |
| 26/Jun-28/Jun | Leukemia Cup Regatta (More...) | Houston, TX, US | |
| 26/Jun-28/Jun | Powerboat Poker Run on the Bay (More...) | Annapolis, MD, USA | |
| 26/Jun | Queen's Cup Race (More...) | Milwaukee, WI, USA | |
| 26/Jun-28/Jun | 'Round the Island (More...) | Ft Walton Beach, FL, USA | |
| 27/Jun-28/Jun | Rock The Hammer/RHYC Open (More...) | Hamilton, Ontario, Canada | |
| 28/Jun-12/Jul | Baltic Cup (More...) | Saint-Petersburg, Russia | |
| 28/Jun-04/Jul | Cape Yachts Beneteau Rally (More...) | South Dartmouth , MA, USA | |
| 29/Jun-05/Jul | Eurocard Gotland Runt (More...) | Stockholm, Stockholm, Sweden | |
| 29/Jun-05/Jul | Match Cup Sweden (More...) | Marstrand, Gothenburg, Sweden | |
| 29/Jun-05/Jul | Match Cup Sweden - World Match Racing Tour (More...) | Marstrand, Gothenburg, Sweden | |
| 29/Jun-17/Jul | Transpacific Yacht Race (More...) | Newport Beach, CA, USA | |
| July / 2009 | |||
| 01/Jul-04/Jul | Intervela (More...) | Riva del Garda, Italy | |
| 01/Jul-28/Jul | Tour de France à la Voile (More...) | Around France, France | |
| 02/Jul-05/Jul | Robbe & Berking mR Sterling Cup 2009 (More...) | Flensburg / Gluecksburg, Schleswig-Holstein, Germany | |
| 03/Jul-04/Jul | 42nd Annual Marina del Rey to San Diego Race (More...) | Marina del Rey & San Diego, CA, USA | |
| 03/Jul-04/Jul | Lake Huron International Regatta (More...) | Port Huron, MI, USA | |
| 03/Jul-03/Jul | Leukemia Cup Regatta (More...) | Traverse City, MI, USA | |
| 04/Jul-06/Jul | 14th Waller-Harris Jersey 2-handed Triangle Race (More...) | , Jersey | |
| 04/Jul-11/Jul | J 80 World Championship 2009 (More...) | Santander, Spain | |
| 04/Jul-11/Jul | Rolex Baltic Week & Star Class European Championship (More...) | Kiel, Schleswig-Holstein, Germany | |
| 04/Jul-12/Jul | Warnemunder Woche (More...) | Rostock, Warnemunde, Germany | |
| 05/Jul | Marblehead-to-Halifax Ocean Race (More...) | Boston, MA, USA | |
| 05/Jul-11/Jul | ORC International Offshore World Championship (More...) | Brindisi, BR, Italy | |
| 05/Jul-11/Jul | Rolex Ilhabela Sailing Week (More...) | Ilhabela, Sao Paulo, Brazil | |
| 06/Jul-11/Jul | U.S. Junior Women's Doublehanded Championship (Ida Lewis Trophy) (More...) | Hampton, VA, USA | |
| 07/Jul-01/Sep | 48th Annual GPSC Sundown - Summer Series (More...) | Grosse Pointe Park, MI, USA | |
| 07/Jul-12/Jul | RC 44 Malcesine SLAM Cup 2009 Continental Challenge (More...) | Malcesine, Lake Garda, Italy | |
| 09/Jul-12/Jul | Volvo Dun Laoghaire Regatta (More...) | Dublin, Dun Laoghaire, Ireland | |
| 09/Jul-18/Jul | Volvo Youth Sailing ISAF World Championship (More...) | Buzios, Rio de Janeiro, Brazil | |
| 10/Jul | Cowes-Dinard-St Malo Race (More...) | Cowes, Isle of Wight, United Kingdom | |
| 10/Jul-10/Jul | Diabetes Research Institute Sail for the Cure Regatta (More...) | Amityville, NY, USA | |
| 10/Jul-12/Jul | Leukemia Cup Regatta (More...) | Deltaville, VA, USA | |
| 10/Jul-19/Jul | RSYC Regatta (More...) | Singapore, Singapore, Singapore | |
| 10/Jul-12/Jul | XX Regata dos Portos dos Descobrimentos Lagos-Palos de La Frontera (More...) | Lagos / Palos de La Frontera, Algarve / Andalucía, Portugal | |
| 11/Jul-12/Jul | Annual Fogh Boorman (More...) | Hamilton, Ontario, Canada | |
| 11/Jul-12/Jul | Cross Border One Design (CBOD) (More...) | Mississauga, Ontario, Canada | |
| 11/Jul | Mayor's Cup Regatta (More...) | Plattsburgh, NY, USA | |
| 11/Jul-12/Jul | Meigs Regatta (More...) | Ft Walton Beach, FL, USA | |
| 11/Jul | Durham, NH, USA | ||
| 11/Jul-17/Jul | Swan European Regatta (More...) | Cowes, Isle of Wight, United Kingdom | |
| 11/Jul-12/Jul | US Shark 24 Championship (More...) | Dunkirk, NY, USA | |
| 11/Jul-12/Jul | US-IRC Great Lakes Championships (More...) | Port Huron, MI, USA | |
| 12/Jul-17/Jul | Whidbey Island Race Week (More...) | Oak Harbor, WA, USA | |
| 13/Jul-18/Jul | Dragon Grand Prix Germany (More...) | Strande/ Kiel, Schleswig-Holstein, Germany | |
| 14/Jul-19/Jul | Governor's Cup 43rd Junior Match Racing Championship (More...) | Newport Beach, CA, USA | |
| 14/Jul-14/Jul | Make A Mark Celebration (More...) | Charlestown, MA, USA | |
| 15/Jul-19/Jul | Swan 42 North American Championship (More...) | Harbour Court, Newport, RI, USA | |
| 16/Jul-19/Jul | Leukemia Cup Regatta (More...) | Rocky River, OH, USA | |
| 17/Jul-19/Jul | 2009 Vineyard Cup (More...) | Vineyard Haven, MA, US | |
| 17/Jul-19/Jul | 2009 Vineyard Cup (More...) | Vineyard Haven, MA, USA | |
| 17/Jul-24/Jul | Hobie 16 North American Championship (More...) | Kingston, ONT, Canada | |
| 17/Jul-17/Jul | Leukemia Cup Regatta (Junior Regatta) (More...) | Beachwood, NJ, USA | |
| 17/Jul-21/Jul | Travemunder Woche Y.C. (More...) | Travemunde, Lubeck Bay, Germany | |
| 17/Jul-19/Jul | Vineyard Cup (More...) | Vineyard Haven, MA, USA | |
| 18/Jul | Chicago Mackinac Island Race (More...) | Chicago, IL, USA | |
| 18/Jul | Edey & Duff 2009 Builder's Cup (More...) | Mattapoisett, MA, USA | |
| 18/Jul | Lake Ontario 300 (More...) | Mississauga, Ontario, Canada | |
| 18/Jul-19/Jul | Park City Regatta (More...) | Briedgeport, CT, USA | |
| 18/Jul-19/Jul | Red Grant Regatta (More...) | Perth Amboy, NJ, USA | |
| 18/Jul-19/Jul | Stolze Cup, LYRA Match Racing Championships (More...) | Toronto, Ontario, Canada | |
| 18/Jul | The Hook Race (More...) | Racine, WI, USA | |
| 18/Jul-19/Jul | The Stolze Cup, 2009 LYRA Match Racing Championships (More...) | Toronto, Ontario, Canada | |
| 19/Jul | FYC / BRYC Invitational Regatta (More...) | Bridgeport, CT, USA | |
| 19/Jul-21/Jul | Screwpile Lighthouse Challenge 2009 (More...) | Solomons, MD, USA | |
| 19/Jul-24/Jul | U.S. Junior Women's Singlehanded Championship (Leiter Trophy) (More...) | Remsenburg, NY, USA | |
| 22/Jul-26/Jul | FujiSankei Business i Waikiki Offshore Series (More...) | Honolulu, Hawaii, USA | |
| 22/Jul-26/Jul | Shipmate Classic Yacht Regatta (More...) | Hellevoetsluis, Zuid Holland, The Netherlands | |
| 22/Jul-26/Jul | Shipmate Classic Yacht Regatta (More...) | Hellevoetsluis, Z-H, Netherlands | |
| 22/Jul-26/Jul | Six Senses Phuket Raceweek (More...) | Rawai, Phuket, Thailand | |
| 23/Jul-26/Jul | Marblehead Sperry Top-Sider NOOD Regatta (More...) | Marblehead, MA, USA | |
| 23/Jul-26/Jul | Techno 293 Junior Windsurfing National Championships (More...) | Hood River, OR, USA | |
| 24/Jul-26/Jul | Cal 25 Class Championship (More...) | Long Beach, CA, USA | |
| 25/Jul | Bayview Mackinac Island Race (More...) | Port Huron, MI, USA | |
| 25/Jul | Chautauqua Corinthian Regatta (More...) | Lakewood, NY, USA | |
| 25/Jul | Leukemia-Lymphoma Society Benefit Regatta (More...) | Bemus Point, NY, USA | |
| 25/Jul | Taylor Trophy (More...) | Southport, CT, USA | |
| 25/Jul | The 100-Miler (More...) | Menominee, MI, USA | |
| 25/Jul-26/Jul | Youngstown Level Regatta (More...) | Youngstown, NY, USA | |
| 25/Jul-26/Jul | Youngstown Level Regatta (More...) | Youngstown, NY, USA | |
| 29/Jul-31/Jul | Techno 293 Junior North American Windsurfing Champs (More...) | San Francisco, CA, USA | |
| 30/Jul-02/Aug | U.S. Singlehanded Championship (O'Day Trophy) (More...) | Detroit, MI, USA | |
| 31/Jul-02/Aug | Aldo Alessio Perpetual Trophy (More...) | San Fancisco Yacht Club, CA, USA | |
| 31/Jul-02/Aug | Dillon Open (More...) | Dillon , CO, USA | |
| 31/Jul-02/Aug | Dillon Open Regatta (More...) | Dillon, CO, USA | |
| 31/Jul-02/Aug | Dillon Open Regatta presented by Audi (More...) | Dillon , CO, USA | |
| 31/Jul-03/Aug | North American Challenge Cup (More...) | Chicago, IL, USA | |
| August / 2009 | |||
| 01/Aug-08/Aug | Copa del Rey (More...) | Palma de Mallorca, Balearic Islands, Spain | |
| 01/Aug-08/Aug | Cowes Week (More...) | Cowes, Isle of Wight, United Kingdom | |
| 01/Aug-06/Aug | CYA Canadian Youth Sailing Championships (More...) | Victoria, BC, Canada | |
| 01/Aug | McNish Classic Race 32nd Year (More...) | Oxnard - Channel Islands Harbor, CA, USA | |