| Season | Helm | Crew | Boat | Venue |
|---|---|---|---|---|
| 2026 | Thomas Burton | M-9 | ||
| 2025 | Robby Wilkins | SC-55 | ||
| 2024 | Sam Rogers | M-42 | ||
| 2022 | Robby Wilkins | SC-55 | ||
| 2020 | Jack Brown | SS-11 | ||
| 2019 | Brian Porter | I-49 | ||
| 2018 | Harry Melges IV | I-1 | ||
| 2017 | Harry Melges IV | I-1 | ||
| 2016 | Harry Melges IV | I-1 | ||
| 2015 | Jeff Bonanni | T-73 | ||
| 2014 | Jeff Bonanni | T-73 | ||
| 2013 | Kevin Jewett | KG-111 | ||
| 2012 | Rob Terry | CR-66 | ||
| 2011 | Vincent Porter | I-2 | ||
| 2010 | Brian Porter | I-49 | ||
| 2008 | Eric Johnson | LE-18 | ||
| 2007 | Sam Rogers | M-42 | ||
| 2006 | Mark Beaton | |||
| 2005 | Vincent Porter | I-2 | ||
| 2004 | Eric Johnson | LE-18 | ||
| 2003 | Tom Burton | M-9 | ||
| 2002 | Mike Darrow | |||
| 2001 | Bob Biwer | |||
| 2000 | Brian Porter | I-49 | ||
| 1999 | Chris Jewett | |||
| 1998 | Harry Melges | I-1 | ||
| 1997 | Brian Porter | I-49 | ||
| 1996 | Andy Burdick | I-45 |
Source: e-scow.org. A * marks a note (hover): a correction to the published roll, or where a title came from.
Honour rolls list titles, not results, so they do not feed the ratings. A name links to a sailor profile only where the match is clear.