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