Fred O’Brien Memorial Trophy
| 2020 Azim Usmanov | 2019 William Aspinwall |
| 2018 Maren Behnke | 2017 Brandon Kwon |
| 2016 Lucas Koenig | 2015 Christopher Moses |
| 2014 Konrad Biedermann | 2013 Colin May |
| 2012 Fesseha Michael | 2011 Max Kahan |
| 2010 Peter Gross | 2009 Nina Heller |
| 2008 Tom Mosler | 2007 Dan Kaplan |
| 2006 Trevor Koelsch | 2005 Ian Heller |
| 2004 RC Wheeler | 2003 Jeffrey Epstein |
| 2002 Austin Cohen | 2001 Lukas Edegran |
| 2000 Gregory Azzaretti | 1999 Cornelia Hobbie |
| 1998 Matthew Fleming | 1997 Whitney Waugh |
| 1996 Harriet Thayer | 1995 Eric Barreveld |
| 1994 Patrick Kiley | 1993 Serena Clarke |
| 1992 Daniel Sparacin | 1991 Evan Gillespie |
| 1990 John Mitchell | 1989 Michael Janensch |
| 1988 Beth Feroe | 1987 Leonard Lombardi |
| 1986 Colleen Durkin | 1985 Deric Hetzel |
| 1984 Alix Rosenthal | 1983 Larry Higdon |
| 1982 Andrea Schreiber | 1981 John Zinman |
| 1980 Michael Rosenblatt | 1979 Ralph Kopera |
Joanna and Michael May Aquarius Trophy
| 2020 Alexandra Niarhos | 2019 Christopher Niarhos |
| 2018 Abbey Gura | 2017 Alex Cea |
| 2016 Oliver Ellsworth | 2015 Joshua Austrian |
| 2014 Giulia Cancro | 2013 Alex Cea |
| 2012 Ryder Stolzenberg | 2011 Chris Moses |
| 2010 Jack Skelton | 2009 Peter Gross |
| 2008 Youssef Assad | 2007 Mitchell Wilson |
| 2006 Tom Mosler | 2005 Hallie Voulgaris |
| 2004 Ian Heller | 2003 Alexander D’Attore |
| 2002 Markus Edegran | 2001 Jeffrey Epstein |
| 2000 Lukas Edegran |
Joseph L. Naar Memorial Trophy
| 2020 (no race) | 2019 Lucas Koenig & Brandon Kown |
| 2018 Maren Behnke & Taylor May | 2017 Kurt Biedermann & Christopher Moses |
| 2016 Daniel Setareh & Rachel Setareh | 2015 Kat O’Donald & Peter Gunn |
| 2014 Kat O’Donald & Peter Gunn | 2013 Ben Goldsmith & Max Kahan |
| 2012 Kevin O’Donnell & Ben Yanelli | 2011 Sean D’Attore & Patrick May |
| 2010 Tom Mosler & Sean D’Attore | 2009 Morgan Wheeler & Nina Heller |
| 2008 Ian Heller & Nina Heller | 2007 Ben Goldsmith & Dan Kaplan |
| 2006 Jasper Fox | 2005 Jeff Saalot, William Holder & Christopher Clancy |
| 2004 Jeremy King & Dan Kaplan | 2003 Greg Azzaretti |
| 2002 Jeff Samalot & Thad Cook | 2001 Lukas Edegran |
| 2000 Peter Benedetto |
