Malcolm “Max” Crosby Trophy
Wianno Yacht Club – Wianno Senior Regatta
| Year | Yacht | Skipper |
| 1973 | Glimpse II (112) | John Bentley, Jr. |
| 1974 | The Junk (124) | Stephen C. Morris |
| 1975 | The Junk (124) | Stephen C. Morris |
| 1976 | Cirrus (136) | George P. Edmonds, Jr. |
| 1977 | Molly (158) | Alan T. McDonough |
| 1978 | Kialoa (123) | John C. Kiley, III |
| 1979 | Madeline (148) | George P. Edmonds, III |
| 1980 | Marna (120) | John T. Fallon |
| 1981 | Cirrus (136) | George P. Edmonds, Jr. |
| 1982 | Pertelote (143) | Boardman Lloyd |
| 1983 | Madeline (148) | Richard M. Burnes, Jr. |
| 1984 | Pertelote (143) | Malcolm Lloyd |
| 1985 | Marna (120) | John T. Fallon, Jr. |
| 1986 | Molly (158) | Alan T. McDonough |
| 1987 | Cochenoe (125) | Donald F. Law, Jr. |
| 1988 | Cochenoe (125) | Donald F. Law, Jr. |
| 1989 | Cochenoe (125) | Donald F. Law, Jr. |
| 1990 | Eight Ball (142) | Karl E. Anderson |
| 1991 | Lindy (182) | Alan T. McDonough |
| 1992 | Lindy (182) | Alan T. McDonough |
| 1993 | Turmoil Too (168) [216] | Brooke Seckel |
| 1994 | Marna (120) | John T. Fallon, Jr. |
| 1995 | Cochenoe (125) | Kevin C. Cain & Andrew Pesek |
| 1996 | Escapade (112) | Barry Plunkett, Jr. |
| 1997 | Sea Lyon (174) | Charles M. Lyons |
| 1998 | Chanzia (157) | Lloyd B. McManus |
| 1999 | Cirrus (136) | Holly Edmonds |
| 2000 | Rapparee (177) | Peter L. O’Keeffe |
| 2001 | Lente Festina (184) | G. Kent Plunkett |
| 2002 | Pertelote (143) | Timothy Fulham |
| 2003 | Cirrus (136) | Holly Edmonds |
| 2004 | Lindy (182) | David McDonough |
| 2005 | Cochenoe (197) | John Kiley |
| 2006 | Heritage (199) | John T. Fallon, Jr. |
| 2007 | Aurora (200) | Holly Edmonds |
| 2008 | Eowyn (202) | George Largay |
| 2009 | Heritage (199) | John T Fallon, Jr. |
| 2010 | Cochenoe (187) | John C Kiley, III |
| 2011 | Mad Jack (206) | Jack Hamilton |
| 2012 | Mad Jack (206) | Jack Hamilton |
| 2103 | Heritage (199) | John T Fallon, Jr. |
| 2014 | Eowyn (202) | Timothy Wadlow |
| 2015 | Scout (220) | Sophie Pesek |
| 2016 | Mad Jack (206) | Jack Hamilton |
| 2017 | Mad Jack (206) | Jack Hamilton |
| 2018 | Smoke (214) | Joe Lotuff |
| 2019 | Mad Jack (206) | Jack Hamilton |
| 2020 | Not Sailed | Covid-19 Pandemic |
| 2021 | Smoke (214) | Jack Howard |
| 2022 | Novanglus (191) | Greg Dempsey |
| 2023 | Aria (213) | Tim Fulham |
| 2024 | Scout (220) | Fraser Pesek |
| 2025 | Scout (220) | Fraser Pesek |