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