Rollins Bowl - Donated by Charles D. Rollins and WM C. PIckford, May 26, 1962
| Year | Sailor Name(s) | Boat Name | Boat Type | Results |
|---|---|---|---|---|
| 2023 | Caleb Paine/Bryan O'Mahoney | |||
| 2022 | Nick Madigan/Mark Strube, NHYC | |||
| 2021 | George Szabo/Isao Toyama, SDYC | |||
| 2019 | Erik Lidecis/Greg Smith, BCYC | |||
| 2017-2018 | Eric Doyle/Payson Infelise, SDYC | |||
| 2016 | Andy MacDonald/Brad Nichol, SSC | |||
| 2013-2015 | George Szabo/Craig Moss, SDYC | |||
| 2012 | Eric Doyle/Steve Brown, SDYC | |||
| 2011 | George Szabo/Mark Strube, SDCC | |||
| 2010 | Mark Reynolds/Hal Haenel, SDYC | |||
| 2009 | Rod Hagebol/Conrad Brown, GGYC | |||
| 2008 | Macdonald/Faith, NHYC | |||
| 2007 | Lidecis/Marzahl, BCYC | |||
| 2006 | Gould/Sieck, StFYC | |||
| 2005 | Lidecis/Marzahl, BCYC | |||
| 2004 | Buckingham/Sperry, NHYC | |||
| 2003 | Brun/Terhaar, SDYC | |||
| 2002 | Beashel/Giles, RPAYC | 7828 | ||
| 2001 | Brun/Dorgan, SDYC | Giselle | ||
| 1997-1998 | Mark Reynolds/Hal Haenel, SDYC | Bongo Fury | ||
| 1996 | Rod Davis/Steve Erickson, CYC/New Zealand | 7525 | ||
| 1995 | Doyle/Terhaar, SDYC | |||
| 1994 | Haines/Kinney, NHYC | |||
| 1993 | Reynolds/Schreiner, SDYC | |||
| 1992 | Vince Brun, SDYC | Giselle | ||
| 1991 | Vince Brun, SDYC | |||
| 1990 | Vince Brun, SDYC | Anna | ||
| 1989 | Vince Brun & Koel Kew, SDYC | |||
| 1987-1888 | Vince Brun & Hugo Schreiner, SDYC | |||
| 1986 | Mark Reynolds & Hal Haenel, SDYC | |||
| 1983-1985 | Mark Reynolds & Hugo Schreiner, SDYC | |||
| 1982 | Iaian Woolword & John Maddocks, StFYC | 6707 "Lion Rampant" | ||
| 1981 | Tom Blackaller & David Shaw, StFYC | 6450 'Faster Horses" | ||
| 1980 | Tryge Liljestrand & Scott Zagarino, CYC | Trigger-Happy II | ||
| 1979 | Barton Beek & Bill Munster, NHYC | Suzanne | ||
| 1977 | Pete Bennet & Kim Fletcher, SDYC | Tranquil | ||
| 1976 | Pete Bennett/Kim Fletcher & Dennis Conner/Carlos Monte & Robby Haines/Arnold Straume | |||
| 1975 | Barton Beek & Bill Munster, NHYC | Suzanne | ||
| 1974 | Malin Burnham & John Burnham, SDYC | Sanctuary | ||
| 1973 | Lowell North & Peter Barrett, SDYC | North Star | ||
| 1972 | Pete Bennett & Kim Fletcher, SDYC | Frolic | ||
| 1970-1971 | Dennis Connor & Jim Reynolds, SDYC | Menace | ||
| 1969 | Chuck Lewsadder & Bill Munster, NHYC | Zucker Kaninchen | ||
| 1968 | Malin Burnham & Tom Skahill, SDYC | Chatterbox | ||
| 1967 | Pete Bennett & Mickey Shanahan, SDYC | Inchmaree | ||
| 1965-1966 | Malin Burnham & Jim Reynolds, SDYC | Chatterbox | ||
| 1964 | Lowell North & Thomas Skahill, SDYC | North Star | ||
| 1963 | John Rumsey & Bob Andre, SDYC | Broadminded | ||
| 1962 | Skip Allan & Bud Cassidy, NHYC | Shadow |