Beginner with the best sportsmanship, enthusiasm, and seamanship.
Original Trophy: Pacific Yacht Club, Rear Commodore Deeds Trophy: Class A, Island Cruise. Won by Aeolus, Captain Frank K. Wyatt, on September 15, 1912. Re-deeded in 1987.
| Year | Sailor Name(s) | Boat Name | Boat Type | Results |
|---|---|---|---|---|
| 2022 | William Simpson | |||
| 2021 | Lorelei Heim | |||
| 2019 | Garett Gardner | |||
| 2018 | Katherine Fleming | |||
| 2017 | Harrison Strom | |||
| 2016 | Anton Schmid | |||
| 2015 | Nikolai Hallsdorson | |||
| 2014 | Mackenzie Harris | |||
| 2013 | Sara Parker | |||
| 2012 | Paulo Campbell | |||
| 2011 | Millie Dorgan | |||
| 2010 | Jack Egan | |||
| 2009 | Ella Frazee | |||
| 2008 | Halea Holasek | |||
| 2007 | Harrison Miller | |||
| 2006 | Casey Ferguson | |||
| 2005 | Casey Hutcheson | |||
| 2004 | Taylor Held | |||
| 2003 | Scott Sinks | |||
| 2002 | Nick Ruppert | |||
| 2001 | Amanda Martin | |||
| 2000 | Chase Gerwin | |||
| 1999 | Jack Driscoll | |||
| 1998 | Sammy Weisman | |||
| 1997 | Willie Weisman | |||
| 1996 | Nick Martin | |||
| 1995 | Lindsey Stewart | |||
| 1994 | Stephen Evanco | |||
| 1993 | Blake Richards | |||
| 1992 | Andy Stewart | |||
| 1991 | Erik Elander | |||
| 1990 | Logan Ott | |||
| 1989 | Kelly Crafton | |||
| 1998 | Molly O'Bryan | |||
| 1987 | Lissa Springstead |