Past winners World's Longest Sunfish Race Around Shelter Island, NY
| Year | # | Event | Venue | Winner |
|---|---|---|---|---|
| 2019 | 49 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Eckart, John |
| 2018 | 48 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Eckart, John |
| 2017 | 47 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Koehler, Jim |
| 2016 | 46 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Montes, Lee |
| 2015 | 45 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Condon, John |
| 2014 | 44 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | McGinnis, Brian |
| 2013 | 43 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Condon, John |
| 2012 | 42 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Boger, Bobby |
| 2011 | 41 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Boger, Bobby |
| 2010 | 40 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Boger, Bobby |
| 2009 | 39 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Heinl, Dick |
| 2008 | 38 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Hines, Bob |
| 2007 | 37 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Condon, John |
| 2006 | 36 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Boger, Bobby |
| 2005 | 35 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Hale, Bart |
| 2004 | 34 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Spicer, Mike |
| 2003 | 33 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Lyman, Keith |
| 2002 | 32 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Condon, John |
| 2001 | 31 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Betts III, Bill |
| 2000 | 30 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Klingler, Todd |
| 1999 | 29 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Klingler, Todd |
| 1998 | 28 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Sullivan, Sean |
| 1997 | 27 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Condon, John |
| 1996 | 26 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Houston, Chris |
| 1995 | 25 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Mockridge, Kenny |
| 1994 | 24 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Nannig, Paul |
| 1993 | 23 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Nannig, Paul |
| 1992 | 22 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Lembeck, Bill |
| 1991 | 21 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Heinl, Dick |
| 1990 | 20 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Suter, Larry |
| 1989 | 19 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Heinl, Dick |
| 1988 | 18 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Sullivan, Shane |
| 1987 | 17 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Heinl, Dick |
| 1986 | 16 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Sullivan, Sean |
| 1985 | 15 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Eckart, John |
| 1984 | 14 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Eckart, John |
| 1983 | 13 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Croasdale, Joe |
| 1982 | 12 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Eckart, John |
| 1981 | 11 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Fisher, Rip |
| 1980 | 10 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Marriner, Blake |
| 1979 | 9 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Meinke, Jeff |
| 1978 | 8 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Fisher, Rip |
| 1977 | 7 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | O'Brien, Mary Beth |
| 1976 | 6 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Sullivan, Joe |
| 1975 | 5 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Fisher, Rip |
| 1974 | 4 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Baldwin, Steve |
| 1973 | 3 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Swan, John |
| 1972 | 2 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Trueman, Don |
| 1971 | 1 | World's Longest Sunfish Race Around Shelter Island, NY | Southold YC | Trueman, Don |
Design & programming: Gerard -Foxbox- Vos (Sunfish NED458)