Based on Junior Invitational, Luff Ins, and Season Series.
Trophy: Awarded to "Anahuac" in1941, for 2nd in Class 3 and 3rd in Class 1.
| Year | Sailor Name(s) | Boat Name | Boat Type | Results |
|---|---|---|---|---|
| 2022 | Olympia Barelli | Sabot | ||
| 2021 | Wyatt Kelly | |||
| 2019 | Charlotte Plant | |||
| 2018 | Devon Owen | |||
| 2017 | Samantha Gardner | |||
| 2016 | Schuyler Capita | |||
| 2015 | Schuyler Capita | |||
| 2014 | Amanda Majernik | |||
| 2013 | Jack Reiter | |||
| 2012 | Jack Egan | |||
| 2011 | Jack Reiter | |||
| 2010 | Charles Lindsay | |||
| 2009 | Charlie Miller | |||
| 2008 | A.J. Reiter | |||
| 2007 | Matt Cappetta | |||
| 2006 | Will LaDow | |||
| 2005 | Edward McCarthy | |||
| 2004 | Nevin Snow | |||
| 2003 | Sam Weisman | |||
| 2002 | Katie Love | |||
| 2001 | Patrick Swan | |||
| 2000 | George Saunders | |||
| 1999 | Nick Martin | |||
| 1998 | Michael Campbell | |||
| 1997 | Adam Roberts | |||
| 1996 | Frank Tybor | |||
| 1995 | Frank Tybor | |||
| 1994 | Bryan Lake | |||
| 1993 | Allison Bell | |||
| 1992 | Andrew Bell | |||
| 1991 | Brian Stanford | |||
| 1990 | Carter Ott | |||
| 1989 | Blair Pruett | |||
| 1988 | Blair Pruett |