| 2019 | 49 | Bonaire | Bonaire Sailing Foundation | 67 | David Misael Hernandez (GTM) |
| 2018 | 48 | Carolina YC (USA) | Carolina YC | 72 | Jean Paul de Trazegnies (PER) |
| 2017 | 47 | Brant Beach, FL (USA) | Brant Beach Yacht Club | 54 | Alonso Collantes de Riglos (PER) |
| 2016 | 46 | Cartagena (COL) | Club Naval | 64 | Alonso Collantes de Riglos (PER) |
| 2015 | 45 | Paracas (PER) | Yacht Club Peruano | 53 | Alexander Zimmermann (PER) |
| 2014 | 44 | Arapahoe, NC (USA) | Camp Sea Gull and Camp Seafarer | 74 | Francisco Renna (ARG) |
| 2013 | 43 | Lewes, DE (USA) | Lewes YC | 74 | Alexander Zimmermann (PER) |
| 2012 | 42 | St. Petersburg, FL (USA) | St Petersburg YC | 74 | Alexander Zimmermann (PER) |
| 2011 | 41 | Curacao | Lions Dive & Beach Resort | 72 | Matheus Dellagnelo (BRA) |
| 2010 | 40 | Italy | Punta Ala | 48 | Jonathan Martinetti (ECU) |
| 2009 | 39 | Bahamas | Nassau YC | 72 | David M. Loring (USA) |
| 2008 | 38 | Ridgeway (CAN) | Buffalo Canoe Club | 72 | Paul Foerster (USA) |
| 2007 | 37 | Brant Beach,FL (USA) | Brant Beach Yacht Club | 100 | Sebastian Mera (DOM) |
| 2006 | 36 | Charleston, SC (USA) | Charleston Harbor Resort and Marina | 100 | David M. Loring (USA) |
| 2005 | 35 | Martinique | Cercle Nautique de Schoelcher | 47 | Lucas Gonzales Smith (ARG) |
| 2004 | 34 | Hyannis, MA (USA) | Hyannis YC | 100 | Eduardo Cordero (USA) |
| 2003 | 33 | St. Maarten | Sint Maarten Yacht Club | 70 | Malcolm Smith (BMU) |
| 2002 | 32 | Houston, TX (USA) | Houston Yacht Club | 64 | Eduardo Cordero (USA) |
| 2001 | 31 | Colonna (Antiqua) | Sunsail Colonna Club | 81 | Eduardo Cordero (USA) |
| 2000 | 30 | Sarasota, FL (USA) | Sarasota Sailing Squadron | 104 | Eduardo Cordero (USA) |
| 1999 | 29 | Puerto Rico | Club Bautico de Ponce | 103 | Eduardo Cordero (USA) |
| 1998 | 28 | Sayville, NY (USA) | Sayville Yacht Club | 100 | Malcolm Smith (BMU) |
| 1997 | 27 | Colombia | Cartagena | 43 | Eduardo Cordero (USA) |
| 1996 | 26 | Dominican Republic | Club Nautica Boca Chica | 75 | Eduardo Cordero (USA) |
| 1995 | 25 | Bahamas | Marsh Harbour Sailing Club | 90 | David M. Loring (USA) |
| 1994 | 24 | Bermuda | Spanish Point Boat Club | 67 | Malcolm Smith (BMU) |
| 1993 | 23 | British Virgin Islands | Virgin Gorda | 65 | Eduardo Cordero (USA) |
| 1992 | 22 | Houston, TX (USA) | Houston Yacht Club | 76 | Paul-Jon Patin (USA) |
| 1991 | 21 | Curacao | Hotel Princess Beach | 93 | Stephen Smeulders (CUW) |
| 1989 | 20 | Orlando, FL (USA) | Orlando YC | 80 | Scott Kyle (USA) |
| 1988 | 19 | Bahamas | Montagu Bay | 73 | Donald Martinborough (BHS) |
| 1987 | 18 | Aruba | Sunfish Club Aruba | 74 | Bruce Sutphen (USA) |
| 1986 | 17 | Barrington (USA) | Barrington YC | 55 | Scott Kyle (USA) |
| 1985 | 16 | Riccione (ITA) | Riccionne | 69 | Donald Martinborough (BHS) |
| 1984 | 15 | Ontario (CAN) | Kingston | 42 | Andy Pimental (USA) |
| 1983 | 14 | Colombia | San Andres island | 73 | Donald Martinborough (BHS) |
| 1982 | 13 | San Mateo, CA (USA) | Coyote Point Yacht Club | 71 | John Kostecki (USA) |
| 1981 | 12 | Baia Sardinia (ITA) | Baia Sardinia | 75 | Dave Chapin (USA) |
| 1980 | 11 | Aruba | Sunfish Club Aruba | 104 | Cor van Aanholt (CUW) |
| 1979 | 10 | Medemblik (NED) | Medemblik | 89 | Dave Chapin (USA) |
| 1978 | 9 | Puerto Rico | Club Bautico de Ponce | 102 | Derrick Fries (USA) |
| 1977 | 8 | Bahamas | Nassau YC | 86 | Pierre Siegenthaler (BHS) |
| 1976 | 7 | Venezuela | Puerto Azul | 70 | Paul Fendler (USA) |
| 1975 | 6 | Miami, FL (USA) | King's Bay | 97 | Derrick Fries (USA) |
| 1974 | 5 | Aruba | Sunfish Club Aruba | 55 | Serge Marsolle (GLP) |
| 1973 | 4 | Martinique | | 97 | Pierre Siegenthaler (BHS) |
| 1972 | 3 | Bermuda | | 45 | Bob Bowles (USA) |
| 1971 | 2 | Venezuela | Puerto Azul | 88 | Ted Moore (USA) |
| 1970 | 1 | US Virgin Islands | St. Thomas YC | 56 | Garry Hoyt (USA) |
