| Year | Call | Name | Boat |
|---|---|---|---|
| 1995 | KE6PH | Barrie Poole | Oceana |
| 1996 | WA5PHO | Joe Banos | Sea Hope |
| 1997 | KE6KDR | Larry Bartholomae | Cherish |
| 1998 | KC6PXN | Tim Tunks | Scallywag |
| 1998 | KD6RGV | Marty Stitt | Cloud Nine |
| 1999 | AE7ML | Mel Langley | T-N-Honey |
| 2000 | NT7E | Stephanie Vermette | U-Betcha |
| 2001 | KB0RIZ | Barbara Campbell | Blue Chablis |
| 2002 | K7GZB | Gene Berg | Sunbear |
| 2003 | KF6IL | Rick Oliviera | Tortuga |
| 2004 | KJ7IV | John Vermette | U-Betcha |
| 2005 | KF6IGY | Fred Thumhart | Sojourn |
| 2006 | KF6GSD | Patrick Malone | Nastalgia |
| 2007 | WB6PKH | Geary Ritchie | El Burro Cove |
| 2008 | KG6RSL | Janice Hawkins | Ceilidh |
| 2009 | K1BGD | Dave Parker | Carlota |
| 2010 | KE7MZB | Jake Howard | Jake |
| 2011 | WB6PHK | Geary Ritchie | El Burro Cove |
| 2012 | KE7DLH | Bob Norquist | The Mile High Island In The Sky |
| 2013 | KG6FSG | Diane Fasel | True Love |
| 2014 | KG6RSM | Jay Hawkins. | Ceilidh |
| 2015 | KG6CQL | Robert Gleser | Harmony |
| 2016 | KJ6MLK | Dan Morrison | Dazzler |
| 2017 | KG7PZO | Bret Mitchell | Liahona |
| 2018 | KG7AVQ | Kirk Doyle | Linger Longer |
| 2018 | N6OLY | Tony Bishop | Dolce |
| 2019 | KF7JLR & KD7VMI | Tom Evans & Annie Naismith | Tappan Zee |
| 2020 | KA6DTC | Don Longfellow | Take Five |
| 2022 | AB7AA | Bill Hickey | Wizzard/Tuscon |