H.L. Ayres Perpetual Trophy | Awarded to the Overall Winner on Corrected Time
| Year | Boat | Owner |
| 1971 | Kahili | Wright / Fricker |
| 1973 | Moonday | G.A. Wolfard |
| 1975 | Ariana | George Thorsen |
| 1977 | Miramar | John Scripps |
| 1979 | Swiftsure | Nick Frazee |
| 1981 | Intrepid | John Delaura |
| 1983 | Celerity | Bill Ostermiller |
| 1985 | Swiftsure | Nick & Robert Frazee |
| 1987 | Ragtime | Pat Farrah |
| 1989 | Silver Bullet | John Delaura |
| 1991 | Silver Bullet | John Delaura |
| 2002 | J-Bird | David Janes |
| 2005 | Peregrine | Simon Garland |
| 2007 | Grand Illusion | Edward McDowell |
| 2009 | Stark Raving Mad V | James Madden |
| 2011 | Horizon | Jack Taylor |
| 2013 | Pyewacket | Roy P. Disney |
| 2015 | Pyewacket | Roy P. Disney |
| 2017 | Grand Illusion | Edward McDowell |
| 2019 | Fast Exit | John Raymont |
State of California - Governor's Trophy | Awarded to the First Boat to Finish
| Year | Boat | Owner |
| 1971 | Aries | Russ Ward |
| 1973 | Ragtime | Kober-Miller-Barney |
| 1975 | Miramar | John Scripps
New Course Record 4D:9H:7M:26S |
| 1977 | Miramar | John Scripps |
| 1979 | Swiftsure | Nick Frazee |
| 1981 | Merlin | Dick Steele |
| 1983 | Merlin | Purdon - Virgilio |
| 1985 | Swiftsure | Nick & Robert Frazee |
| 1987 | Blondie | Robert McNulty |
| 1989 | Taxi Dancer | Mitchell Rouse |
| 1991 | Silver Bullet | John DeLaura |
| 1993 | Persuasion | Neil Barth |
| 2002 | Zephyrus | Robert McNeil
(Isla Navidad Race) |
| 2005 | Magnitude 80 | Doug Baker
New Course Record 2D:13H:25M:58S |
| 2007 | Stark Raving Mad III | James Madden |
| 2009 | Stark Raving Mad IV | James Madden |
| 2011 | Akela | Dave James & John Turpin |
| 2013 | Wizard | David Askew |
| 2015 | Rio 100 | Manouch Mosayedi |
| 2017 | Zephyrus - Monohull
Phaedo 3 - Multihull |
Damon Guizot
Lloyd Thornburg |
| 2019 | Good Call | Tom Barker |
Miguel Aleman | Awarded to the Winner of Class A / ORR 1
| Year | Boat | Owner |
| 1971 | Aries | Russ Ward |
| 1973 | Dorothy "O" | Bob Beauchamp |
| 1975 | Dorothy "O" | Bob Beauchamp |
| 1977 | Miramar | John Scripps |
| 1979 | Swiftsure | Nick Frazee |
| 1981 | Hana Ho | Morrie Kirk |
| 1983 | Hana Ho | Morrie Kirk |
| 1985 | Swiftsure | Nick & Robert Frazee |
| 1987 | Ragtime | Pat Farrah |
| 1989 | Silver Bullet | John Delaura |
| 1991 | Silver Bullet | John Delaura |
| 1993 | Heartbeat | Chuck Brewer |
| 2002 | Zephyrus | Robert McNeil |
| 2005 | Scout Spirit | Bill Turpin |
| 2007 | Peligroso | D. Williams & M. Campbell |
| 2009 | Grand Illusion | Edward McDowell |
| 2011 | Akela | David Jones & Bill Turpin |
| 2013 | Natalie J | Philip O'Neil |
| 2015 | Invisible Hand | Frank Slootman |
| 2017 | Zephyrus | Damon Guizot |
| 2019 | Destroyer | Jim Bailey |
City of Newport Beach Mayor's Trophy | Awarded to the Winner of Class B / ORR 2
| Year | Boat | Owner |
| 1973 | Moonday | G.A. Wolfard |
| 1975 | Ragdoll | John Hall |
| 1977 | Mamie | Milt Smith |
| 1979 | Cadenza | Carl Eichenlaub |
| 1981 | Free Enterprise | Hartley Turpin |
| 1983 | Aleta | Warren Hancook |
| 1985 | Amante | Mel Richley |
| 1987 | Amante | Mel Richley |
| 1989 | Racy II | Luciana Taylor |
| 1991 | Strider | Barbara Colville |
| 1993 | Bay Wolf | Kirk & Jocelyn Wilson |
| 1995 | Persuasion | Neil Barth |
| 2002 | J-Bird III | David Janes (Isla Navidad Race) |
| 2005 | Mongoose | Dennis Conner |
| 2007 | Grand Illusion | Edward McDowell |
| 2009 | Criminal Mischief | Chip Megeeath |
| 2011 | Grand Illusion | Edward McDowell |
| 2013 | Pyewacket | Roy P. Disney |
| 2015 | Pyewacket | Roy P. Disney |
| 2017 | Grand Illusion | Edward McDowell |
| 2019 | Pyewacket | Roy P. Disney |
Awarded to the Winner of Class C / ORR 3
| Year | Boat | Owner |
| 1973 | Kahili | Wright / Fricker |
| 1975 | Ariana | George Thorsen |
| 1977 | Ghost II | John Reynolds |
| 1979 | Renegade | Sandy Purdon |
| 1981 | Shenandoah | Bill Palmer |
| 1983 | Celerity | Bill Ostermiller |
| 1985 | Eclipse | Bannasch / Crouch |
| 1987 | One Eyed Jack | Jim Svetich |
| 1989 | Reliance | Chuck Nichols |
| 1991 | Patriot | Jerry Montgomery |
| 2002 | Bay Wolf | Kirk Wilson
(Isla Navidad Race) |
| 2005 | Reinrag2 | Tom Garnier |
| 2007 | Valkyrie | Andrew Rasdel |
| 2009 | Stark Raving Mad IV | James Madden |
| 2011 | Horizon | Jack Taylor |
| 2013 | Bretwalda 3 | Bob Pethick |
| 2015 | Lucky Duck | Dave MacEwen |
| 2017 | Horizon | John Schulz |
| 2019 | Fast Exit | John Raymont |
James Webster Gaboon | Awarded to the Winner of Class D
| Year | Boat | Owner |
| 2005 | Tabasco | John Wylie |
| 2007 | Picante | Tom Jorgesen |
| 2013 | Dorade | Matt Brooks |
| 2015 | Between the Sheets | Ross Pearlman |
| 2019 | Horizon | John Schulze |
Awarded to the Fastest PHRF Boat on Corrected Time
| Year | Boat | Owner |
| 2013 | Dorade | Matt Brooks |
| 2015 | Between the Sheets | Ross Pearlman |
| 2019 | Chubasco | Baker, Carpenter, Durant |
Awarded to the Winner of Class E / 1st ORCA Multihull
| Year | Boat | Owner |
| 2005 | Peregrine | Simon Garland |
| 2007 | Between the Sheets | Ross Pearlman |
| 2015 | Mighty Merloe Multihull |
H.L. Enloe |
| 2017 | Phaedo 3 Multihull |
Lloyd Thornburg |
| 2019 | Ticket to Ride | Frank Stich |
