Trophies
Awarded each race for the Fastest Monohull Elapsed Time in the race. Originally the "First to Finish" Trophy.
* = Record Holder
| YEAR | BOAT | OWNER/SKIPPER | Elapsed Time |
|---|---|---|---|
| 2023 | Rio 100 | Sebastian Moshayedi | 7 days 13:16:38 |
| 2021 | Pyewacket 70 | Roy P. Disney | 5 days 16:53:20 |
| 2019* | Comanche | Jim Cooney & Samantha Grant | 5 days 11:14:05* |
| 2017 | Rio 100 | Manouch Moshayedi | 6 days 17:09:09 |
| 2015 | Rio 100 | Manouch Moshayedi | 7 days 05:34:07 |
| 2013 | Wizard | Dave Askew | 7 days 07:53:46 |
| 2011 | Bella Mente | Hap Fauth | 6 days 19:44:28 |
| 2009 | Samba Pa Ti | John Kilroy Jr. | 7 days 8:17:11* |
| 2007 | Pyewacket | Roy P. Disney | 7 days 19:08:10 |
| 2005 | Morning Glory | Hasso Plattner | 6 days 16:04:11* |
| 2003 | Pegasus 77 | Philippe Kahn | 7 days 16:31:17 |
| 2001 | Pegasus | Philippe Kahn | 8 days 02:34:03 |
| 1999 | Pyewacket | Roy E. Disney | 7 days 11:41:27* |
| 1997 | Pyewacket | Roy P. Disney | 7 days 15:24:40* |
| 1995 | Cheval 95 | Hal Ward | 9 days 01:32:20 |
| 1993 | Silver Bullet | John DeLaura | 9 days 09:11:17 |
| 1991 | Chance | Robert McNulty | 9 days 21:59:35 |
| 1989 | Silver Bullet | John DeLaura | 8 days 12:50:35 |
| 1987 | Merlin | Donn Campion | 8 days 12:00:40 |
| 1985 | Swiftsure III | Nick/Robert Frazee | 10 days 19:21:47 |
| 1983 | Charley | Nolan K. Bushnell | 9 days 01:53:48 |
| 1981 | Merlin | Nick Frazee | 8 days 11:02:31 |
| 1979 | Drifter | Harry Moloschco | 11 days 18:01:04 |
| 1977 | Merlin | Bill Lee | 8 days 11:01:45* |
| 1975 | Ragtime | White/Pasquini | 9 days 23:54:51 |
| 1973 | Ragtime | Ragtime Syndicate | 10 days 14:00:40 |
| 1971 | Windward Passage | Mark Johnson | 9 days 09:06:48* |
| 1969 | Blackfin | Kenneth DeMeuse | 9 days 10:21:00* |
| 1967 | Stormvogel | Cornelius Bruynzeel | 11 days 14:10:56 |
| 1965 | Ticonderoga | Robert Johnson | 9 days 13:51:02* |
| 1963 | Ticonderoga | Robert Johnson | 11 days 16:46:33 |
| 1961 | Sirius II | Howard F. Ahmanson | 10 days 10:38:35 |
| 1959 | Goodwill | Ralph Larrabee | 10 days 12:16:15 |
| 1957 | Barlovento | Frank Hooykaas | 11 days 13:02:44 |
| 1955 | Morning Star | Richard S. Rheem | 9 days 15:05:10* |
| 1953 | Goodwill | R.E. Larrabee | 11 days 02:17:24 |
| 1951 | Morning Star | Richard S. Rheem | 10 days 16:44:33 |
| 1949 | Morning Star | Richard S. Rheem | 10 days 10:13:09* |
| 1947 | Chubasco | W.L. Stewart Jr. | 12 days 15:51:18 |
| 1941 | Stella Maris | Dr. A. Steele | 13 days 21:03:55 |
| 1939 (SF) | Contender | Richard R. Loynes | 14 days 07:50:00 |
| 1936 (SMon) | Dorade | James Flood | 13 days 07:20:04 |
| 1934 | Vileehi | H.T. Horton | 13 days 03:42:26 |
| 1932 (SB) | Fayth | William S. McNutt | 14 days 14:33:00 |
| 1930 | Enchantress | Morgan Adams | 12 days 13:22:52 |
| 1928 (Balboa) | Talayha | L. Lippman | 13 days 04:58:30 |
| 1926 | Invader | Don M. Lee | 12 days 02:48:03* |
| 1923 (SB) | Mariner | L.A. Norris | 11 days 14:46:00 |
| 1912 | Lurline | A.E. Davis | 13 days 17:03:00 |
| 1910 | Hawaii | Hawaii Syndicate | 14 days 03:23:00 |
| 1908 | Lurline | H.H. Sinclair | 13 days 21:31:00 |
| 1906 | Lurline | H. H. Sinclair | 12 days 09:59:00 |