| NEWPORT HARBOR | |||
| Year | Skipper | Boat Name | Club |
| 2023 | Rosene Family | Radical Departure | BYC |
| 2022 | Rosene Family | Radical Departure | BYC |
| 2021 | Richley Family | Amante | NHYC & LIYC |
| 2020 | Richley Family | Amante | NHYC & LIYC |
| 2019 | Ray Booth | Altheris | BYC |
| 2018 | Brian & Betsy Dougherty | Legacy | BYC |
| 2017 | Brian & Betsy Dougherty | Legacy | BYC |
| 2016 | Brian & Betsy Dougherty | Legacy | BYC |
| 2015 | Buddy Richley | Amante | LIYC |
| 2014 | Buddy Richley | Amante | LIYC |
| 2013 | Buddy Richley | Amante | LIYC |
| 2012 | Roy Jones | Tango | BYC |
| 2011 | John Szalay | Pussy Cat | UCISA |
| 2010 | John Szalay | Pussy Cat | UCISA |
| 2009 | Joe Degenhardt | Lickity Split | BCYC |
| 2008 | Andrew Donchak | Rapid Transit | BYC |
| 2007 | David Gray | Pendragon | BCYC |
| 2006 | Bill Taylor | Scavenger | BYC |
| 2005 | David Gray | Pendragon | BCYC |
| 2004 | David Gray | Pendragon | BCYC |
| 2003 | Denis Rosene | Sorcerer | BYC |
| 2002 | Bill Taylor | Scavenger | BYC |
| 2001 | Denis Rosene | Sorcerer | BYC |
| 2000 | Denis Rosene | Sorcerer | BYC |
| 1999 | Joe Degenhardt | Lickity Split | BCYC |
| 1998 | Jim Kerrigan | Eris | BCYC |
| 1997 | Rico Braggins | SSYC | |
| 1996 | Rod Woods/Jim Kerrigan | Jiffy Too | BCYC |
| 1995 | Joe Degenhardt | Lickity Split | BCYC |
| 1994 | Not Awarded | ||
| 1993 | Not Awarded | ||
| 1992 | Rod Woods/Jim Kerrigan | Jiffy Too | BCYC |
| 1991 | Chuck Holand | Amorous | BCYC |
| 1990 | Chuck Holand | Amorous | BCYC |
| DANA POINT HARBOR | |||
| Year | Skipper | Boat Name | Club |
| 2023 | Bobby Walker | Amadeus | DPYC |
| 2022 | Bobby Walker | Amadeus | DPYC |
| 2021 | Norman D Hosford | Chaos Theory | DPYC |
| 2020 | Brian Nickel | Blitz | NHYC |
| 2019 | Jock & Lily McGraw | Tekeela | DWYC |
| 2018 | Scott Clapp & Jeremy Quinton | Gray Goose | DPYC |
| 2017 | Scott Clapp & Jeremy Quinton | Gray Goose | DPYC |
| 2016 | Scott Clapp & Jeremy Quinton | Gray Goose | DPYC |
| 2015 | Ed Kooij | Occam's Razor | DPYC |
| 2014 | Viggo Torbensen | Time Shaver | DPYC |
| 2013 | Brian & Chris Werner | Ruckus | DPYC |
| 2012 | Steve Wyamn | Nahunu | DPYC |
| 2011 | Bruce Lotz | DPYC | |
| 2010 | Viggo Torbenson | Martella | SBYRC |
| 2010 | Viggo Torbenson | Martella | SBYRC |
| 2009 | Viggo Torbenson | Martella | SBYRC |
| 2008 | Viggo Torbenson | Martella | SBYRC |
| 2007 | Viggo Torbenson | Martella | SBYRC |
| 2006 | Viggo Torbenson | Martella | SBYRC |
| 2005 | Viggo Torbenson | Martella | SBYRC |
| 2004 | Viggo Torbenson | Martella | SBYRC |
| 2003 | Viggo Torbenson | Martella | SBYRC |
| 2002 | Ted Mays | Ouch! | DPYC |
| 2001 | Paul Wager | Radical Departure | DPYC |
| 2000 | Harrel Jones | Cool Man Cool | DWYC |
| 1999 | Harrel Jones | Cool Man Cool | DWYC |
| 1998 | Barry & Sue Senescu | Rattle & Humm | DPYC |
| 1997 | Bob Laird/Bob Walker | Jalapena | DPYC |
| 1996 | Carlos Williams | Tie Breaker | CBYC |
| 1995 | Not Awarded | ||
| 1994 | Not Awarded | ||
| 1993 | Not Awarded | ||
| 1992 | Murray Jameson | Slingshot | CBYC |
| 1991 | Ralph Cameron | Raz-Ma-Taz | DPYC |
| 1990 | Bruce Lotz | Anticipation | DPYC |