Wianno Yacht Club Regatta
Ocean Race Trophy
Presented by Mr. and Mrs. C.P. Mayer
| Year | Yacht | Skipper |
| 1959 | Marna (120) | John T. Fallon |
| 1960 | Kim (75) | William S. Kimball |
| 1961 | Marna (120) | John T. Fallon |
| 1962 | West Wind (113) | Peter T. Damon |
| 1963 | West Wind (113) | Peter T. Damon |
| 1964* | Marna (120) | John T. Fallon |
| 1965 | Venture (85) | David D. Steere |
| 1966 | Cirrus (136) | George P. Edmonds, Jr. |
| 1967 | Cirrus (136) | George P. Edmonds, Jr. |
| 1968 | Cirrus (136) | George P. Edmonds, Jr. |
| 1969 | Bettawin (141) | Ross W. Richards |
| 1970 | Marna (120) | John T. Fallon |
| 1971 | Cirrus (136) | George P. Edmonds, Jr. |
| 1972 | Venture (85) | David D. Steere |
| 1973 | Invader (134) | Lewis J.H. Gunn |
| 1974 | No Race – High Winds | |
| 1975 | Invader (169) | Lewis J.H. Gunn |
| 1976 | We’re Here (129) | Connie M. Tracy |
| 1977 | Invader (169) | Lewis J.H. Gunn |
| 1978 | Invader (169) | Lewis J.H. Gunn |
| 1979 | Cirrus (136) | George P. Edmonds, Jr. |
| 1980 | Invader (169) | Lewis J.H. Gunn |
| 1981 | Pertelote (143) | Francis V. Lloyd, III |
| 1982 | Pertelote (143) | Boardman Lloyd |
| 1983 | Cochenoe (143) | Donald F. Law, Jr. |
| 1984 | Steamer (163) [173] | Thomas H. O’Toole |
| 1985 | Snow Goose (161) | Lewis J.H. Gunn |
| 1986 | Molly (158) | Alan T. McDonough |
| 1987 | Scarlet (163) [173] | Thomas H. O’Toole |
| 1988 | Invader (174) | Lewis J.H. Gunn |
| 1989** | Cochenoe (125) | Donald F. Law, Jr. |
| 1990 | Eight Ball (142) | Karl E. Anderson |
| 1991 | Cirrus (136) | Holly Edmonds |
| 1992 | Cirrus (136) | Alden Edmonds |
| 1993 | Invader (184) | Lewis J.H. Gunn |
| 1994 | Eight Ball (142) | Karl E. Anderson |
| 1995 | No Race – High Winds | |
| 1996 | Marna (120) | John T. Fallon, Jr. |
| 1997 | Lindy (182) | David McDonough |
| 1998 | Invader (161) | Lewis J.H. Gunn |
| 1999 | Rapparee (177) | Peter L. O’Keeffe |
| 2000 | Chanzia (157) | Lloyd B. McManus, Jr. |
| 2001 | Pieces of 8 (188) | Karl E. Anderson |
| 2002 | Pieces of 8 (188) | Karl E. Anderson |
| 2003 | Pieces of 8 (188) | Karl E. Anderson |
| 2004 | Pieces of 8 (188) | Todd Kittredge |
| 2005 | Eowyn (202) | George Largay |
| 2006 | Heritage (199) | John T. Fallon, Jr. |
| 2007 | Yankee Dime (150) | Frank Saul |
| 2008 | Mad Jack (206) | Jack Hamilton |
| 2009 | Lindy (182) | David McDonough |
| 2010 | Pieces of 8 (188) | Heather Gregg |
| 2011 | Heritage (199) | John T. Fallon, Jr. |
| 2012 | Beltane (222) | Jim Cunningham |
| 2013 | Madeline (207) | Gordon Burnes |
| 2014*** | Heritage (199) | John T Fallon, Jr. |
| 2015 | Mad Jack (206) | Jack Hamilton |
| 2016 | Scout (220) | Kelsey Wheeler |
| 2017 | Kerplunk (184) | Kent Plunkett |
| 2018 | Kerplunk (184) | Kent Plunkett |
| 2019 | Madeline (207) | Eli & Henry Burnes |
| 2020 | Aria (213) | Mary Fulham |
| 2021 | Mad Jack (206) | Jack Hamilton |
| 2022 | Race Abandoned | No wind |
| 2023 | Aria (213) | Peter Shope |
| 2024 | Aria (213) | Peter Shope |
| 2025 | Smoke (214) | Joe Lotuff |
* Fiftieth Anniversary Regatta Trophy Awarded in lieu of Ocean Race Trophy.
** 75th Anniversary Weekend
*** 100th Anniversary Weekend