Hyannis Yacht Club Regatta
Winners of First Race, 1954 – 1958
| Year | Yacht | Skipper |
| 1954 | Alert (87) | Richard P. O’Leary |
| 1955 | No Race | |
| 1956 | No Record | |
| 1957 | Venture (85) | David D. Steere |
| 1958 | Mimi (36) | Dora S. Loutrel |
Winners of Second Race, 1954 – 1958
| Year | Yacht | Skipper |
| 1954 | Venture (85) | David D. Steere |
| 1955 | No Race | |
| 1956 | No Record | |
| 1957 | Bettayet (117) | Ross W. Richards |
| 1958 | Uncle Benny (73) | Connie Moore |
Hyannis Yacht Club Trophy
| Year | Yacht | Skipper |
| 1990 | Eight Ball (142) | Karl E. Anderson |
| 1991 | Cochenoe (125) | Kevin C. Cain |
| 1992 | Cirrus (136) | Alden Edmonds |
| 1993 | Althaea (185) | Richard M. Burnes, Jr. |
| 1994 | Eight Ball (142) | Karl E. Anderson |
| 1995 | Marna (120) | John T. Fallon, Jr. |
| 1996 | Cirrus (136) | Holly Edmonds |
| 1997 | Rapparee (177) | Peter L. O’Keeffe |
| 1998 | Cirrus (136) | Holly Edmonds |
| 1999 | Eight Ball (142) | Karl E. Anderson |
| 2000 | Scarlet (163) [173] | Burt McManus |
| 2001 | Pieces of 8 (188) | Karl E. Anderson |
| 2002 | Yankee Dime (145) | B. Francis Saul, III |
| 2003 | Yankee Dime (145) | B. Francis Saul, III |
| 2004 | Pieces of 8 (188) | Todd Kittredge |
| 2005 | Yankee Dime (150) | Joseph Lotuff |
| 2006 | Dauntless (195) | Jeffrey Tracy |
| 2007 | Dauntless (195) | Bradford Tracy |
| 2008 | Dauntless (195) | Jeffrey Tracy |
| 2009 | Mad Jack (206) | Jack Hamilton |
| 2010 | Smoke (214) | B. Francis Saul, III |
| 2011 | Eowyn (202) | Tim Wadlow |
| 2012 | Beltane (222) | Jim Cunningham |
| 2013 | Madeline (207) | Gordon Burnes |
| 2014 | Madeline (207) | Gordon Burnes |
| 2015 | Eowyn (202) | Timothy Wadlow |
| 2016 | Scout (220) | Kelsey Wheeler |
| 2017 | Eowyn (202) | Tim Wadlow |
| 2018 | Mad Jack (202) | Jack Hamilton |
| 2019 | Madeline (207) | Eli & Henry Burnes |
| 2020 | Patience (179) | Benjamin Blum |
| 2021 | Patience (179) | Benjamin Blum |
| 2022 | Race Abandoned | |
| 2023 | Patience (179) | Benjamin Blum |
| 2024 | Kerplunk (225) | Kent Plunkett |
| 2025 | Aria (213) | Peter Shope |