Wianno Yacht Club Long Distance Race
Race Winners
| Year | Yacht | Skipper |
| 1916 | Fantasy (11) | James G. Hinkle |
| 1917 | No Record | |
| 1918 | Ethyl (14) | Melville |
| 1919 | No Record |
Long Distance Challenge Cup
Presented by Commodore Edward C. Crossett
(Trophy Retired by James G. Hinkle)
| Year | Yacht | Skipper |
| 1920 | A.P.H. (4) | W.P. Halliday |
| 1921 | Fantasy (11) | James G. Hinkle |
| 1922 | Tomboy (22) | Edward C. Crossett |
| 1923 | Fantasy (11) | James G. Hinkle |
| 1924 | Wendy (2) | Henry B. Day |
| 1925 | Water Nymph (33) | Fritz B. Talbot |
| 1926 | A.P.H. (4) | W.P. Halliday |
| 1927 | Tomboy (22) | Edward C. Crossett |
| 1928 | Ethyl (14) | Robert M. Roloson |
| 1929 | Wendy (2) | Henry B. Day |
| 1930 | Malolo (60) | Harry F. Stimpson |
| 1931 | Malolo (60) | Harry F. Stimpson |
| 1932 | Tomboy (22) | Edward C. Crossett |
| 1933 | Venture (85) | David D. Steere |
| 1934 | Gull (21) [28] | C. McGregory Wells |
| 1935 | Moby Dick (91) | William R. Scott |
| 1936 | Quip (101) | Mrs. Kenneth Boyd |
| 1937 | Fiddler (1) [37] | Mary Parlett |
| 1938 | Jolly Roger (101A) [25] | James A. Waller |
| 1939 | El Cid II (114) | John C. Kiley, Jr. |
| 1940 | Jivaro (81) | P. & D. Bauder |
| 1941 | Cave Canum (82) | Joseph P. Carney |
| 1941-1945 | No Races | |
| 1946 | Fantasy (11) | James G. Hinkle |
‘Tween Waters Trophy
Presented by Commodore John W. Hornor
(Retired by John C. Kiley, Jr.)
| Year | Yacht | Skipper |
| 1947 | El Cid II (114) | John C. Kiley, Jr. |
| 1948 | Commy (5) | John Shafroth |
| 1949 | West Wind (113) | W.W. Sinclaire |
| 1950 | El Cid II (114) | John C. Kiley, Jr. |
| 1951 | Kypris (84) | Joseph Mattison, Jr. |
| 1952 | Kypris (84) | Joseph Mattison, Jr. |
| 1953 | Roweida VII (95) | Gordon R. Beggs |
| 1954 | El Cid II (114) | John C. Kiley, Jr. |
| 1955 | Fire Chief (105) | Vincent R. Bailey |
| 1956 | Commy (5) | John Shafroth |
| 1957 | Bettayet (117) | Ross Richards |
| 1958 | Dungolphin (109) | Durban McGraw |
| 1959 | Marna (120) | John T. Fallon |
| 1960 | Bettayet (117) | Ross Richards |
| 1961 | No Record | |
| 1962 | Venture (85) | David D. Steere |
| 1963 | Sovereign IV (83) | Harrison Bridge |
| 1964 | Venture (85) | David D. Steere |
| 1965 | Venture (85) | David D. Steere |
| 1966 | Victura (94) | Edward M. Kennedy |
| 1967 | Venture (85) | David D. Steere |
| 1968 | Invader (134) | Lewis J.H. Gunn |
| 1969 | No Record | |
| 1970 | Venture (85) | David D. Steere |
| 1971 | No Record | |
| 1972 | Kialoa (123) | John C. Kiley, III |
| 1973 | No Record | |
| 1974 | Pertelote (143) | Boardman Lloyd |
| 1975 | Pertelote (143) | Francis V. Lloyd, III |
| 1976 | Invader (169) | Lewis J.H. Gunn |
| 1977-1978 | No Record | |
| 1979 | Pertelote (143) | Boardman Lloyd |
| 1980 | Cirrus (136) | Alden Edmonds |
| 1981 | No Record | |
| 1982 | Pertelote (143) | Boardman Lloyd |
| 1983-1985 | No Record | |
| 1986 | Molly (158) | Alan T. McDonough |
| 1987 | Victura (167) [194] | Edward M. Kennedy |
| 1988 | Cirrus (136) | Holly Edmonds |
James G. Hinkle Long Distance Trophy
1920 Crossett Trophy Placed Back in Competition by the Hinkle Family
| Year | Yacht | Skipper |
| 1989 | Cochenoe (125) | Andrew Pesek |
| 1990 | Marna (120) | John T. Fallon, Jr. |
| 1991 | Invader (184) | Lewis J.H. Gunn |
| 1992 | Invader (184) | Lewis J.H. Gunn |
| 1993 | Fantasy (137) | Joseph D. Hinkle |
| 1994 | Fantasy (137) | Joseph D. Hinkle |
| 1995 | Molly (158) | John T. McDonough |
| 1996 | Escapade (112) | Barry Plunkett, Jr. |
| 1997 | Cirrus (136) | Holly Edwards |
| 1998 | Chanzia (157) | Lloyd B. McManus, Jr. |
| 1999 | Molly(158) | John T. McDonough |
| 2000 | Yankee Dime (145) | Alden Edmonds |
| 2001 | Lucinda (175) | Chip Niehoff |
| 2002 | Cochenoe (125) | Donald F. Law, Jr. |
| 2003 | Lindy (182) | David McDonough |
| 2004 | Dauntless (195) | Jeffrey Tracy |
| 2005 | Aurora (200) | Karl Anderson |
| 2006 | Dauntless (195) | Jeffrey Tracy |
| 2007 | Mad Jack (206) | Jack Hamilton |
| 2008 | Mad Jack (206) | Jack Hamilton |
| 2009 | Pieces of 8 (188) | John Gregg |
| 2010 | Smoke (214) | Joe Lotuff |
| 2011 | No Race | High Winds |
| 2012 | Aurora (200) | Matt Cannistraro |
| 2013 | Beltane (222) | Jim Cunningham |
| 2014 | Mad Jack (206) | Jack Hamilton |
| 2015 | Eowyn (202) | Timothy Wadlow |
| 2016 | Mad Jack (206) | Jack Hamilton |
| 2017 | Scout (220) | Sophie Pesek |
| 2018 | Eowyn (202) | Tim Wadlow |
| 2019 | Mad Jack (206) | Jack Hamilton |
| 2020 | Not sailed | Covid-19 Pandemic |
| 2021 | Novanglus (191) | Greg Dempsey |
| 2022 | Three Sticks (212) | Peter McAvoy |
| 2023 | Not Sailed | High Winds |
| 2024 | Kerplunk (225) | Kent Plunkett |
| 2025 | Kerplunk (225) | Bob Curran |