| Year | Rider | Horse | Breed | Sex | Age | Time |
|---|---|---|---|---|---|---|
| 1955 | Wendell Robie | Bandos | Arabian | S | 15 | Note: The Lloyd Tevis Cup was first awarded in 1959. Recorded timing began in 1961. |
| 1956 | Wendell Robie | Bandos | Arabian | S | 16 | |
| 1957 | Wendell Robie | Molla | Arabian | M | 9 | |
| 1958 | Wendell Robie | Molla | Arabian | M | 10 | |
| 1959 | Nick Mansfield | Buffalo Bill | TB Cross | G | 11 | |
| 1960 | Ernie Sanchez | Marko B | Mustang | G | 13 | |
| 1961 | Drucilla Barner | Chagitai | 3/4 Arabian | G | 10 | 13:02 |
| 1962 | Paige Harper | Chief of Tahmaroo | 3/4 Arabian | G | 6 | 14:33 |
| 1963 | Pat Fitzgerald | Ken | Arabian | G | 7 | 13:30 |
| 1964 | Neil Hutton | Salalah | Arabian | M | 10 | 14:10 |
| 1965 | Ed Johnson | Bezatal | Arabian | S | 7 | 11:38 |
| 1966 | Bud Dardi | Pancho | 1/2 Arabian | G | 10 | 12:46 |
| 1967 | Ed Johnson | Bezatal | Arabian | S | 8 | 11:42 |
| 1968 | Bud Dardi | Pancho | 1/2 Arabian | G | 12 | 11:18 |
| 1969 | Marion Robie Arnold | Hailla | Arabian | M | 8 | 12:57 |
| 1970 | Donna Fitzgerald | Witezarif | Arabian | G | 7 | 11:49 |
| 1971 | Donna Fitzgerald | Witezarif | Arabian | G | 8 | 12:35 |
| 1972 | Donna Fitzgerald | Witezarif | Arabian | G | 9 | 12:42 |
| 1973 | Donna Fitzgerald | Witezarif | Arabian | G | 10 | 11:53 |
| 1974 | Hal V. Hall | El Karbaj | Arabian | G | 8 | 13:55 |
| 1975 | Donna Fitzgerald | Witezarif | Arabian | G | 12 | 12:04 |
| 1976 (Tie) |
Donna Fitzgerald | Witezarif | Arabian | G | 13 | 11:59 |
| Sam Arnold | R.C. Champ | Arabian | G | 8 | 11:59 | |
| 1977 | Hal V. Hall | El Karbaj | Arabian | G | 11 | 14:15 |
| 1978 | Kathie Perry | Prince Koslaif | Arabian | G | 12 | 12:17 |
| 1979 | Boyd Zontelli | R.C. Eaton | Arabian | G | 9 | 11:33 |
| 1980 | Loreley Stewart | Don Van Witt | Arabian | G | 9 | 12:30 |
| 1981 | Boyd Zontelli | R.C. Hans | Arabian | G | 7 | 10:46 |
| 1982 | Marjorie Pryor | Fritz | Arabian | G | 11 | 14:00 |
| 1983 | Marjorie Pryor | Fritz | Arabian | G | 12 | 12:21 |
| 1984 | Becky Hart | Grand Sultan | Arabian | G | 8 | 13:41 |
| 1985 | Boyd Zontelli | R.C. Hans | Arabian | G | 12 | 14:45 |
| 1986 | Loreley Stewart | Risque Rocket | Arabian | M | 8 | 13:57 |
| 1987 | Kathy Ray | Easter Charm | Arabian | M | 9 | 14:00 |
| 1988 | Becky Hart | Grand Sultan | Arabian | G | 12 | 13:27 |
| 1989 | Lari Shea | Sur Sherif | Arabian | G | 12 | 12:48 |
| 1990 | Hal V. Hall | HCC Zarlusko | Arabian | G | 9 | 15:56 |
| 1991 | Erin McChesney | Cougar's Fete | 3/4 Arabian | M | 9 | 15:19 |
| 1992 (Tie) |
Shellie Hatfield | AM Xanthium | Arabian | M | 9 | 15:30 |
| Marcia Smith | Harry | Arabian | G | 14 | 15:30 | |
| 1993 | Chris Knoch | Saxx | Arabian | G | 7 | 14:44 |
| 1994 | Chris Knoch | Saxx | Arabian | G | 8 | 14:48 |
| 1995 | Matthew Mackay-Smith | W.C. Freiheit | Anglo/Arab | G | 11 | 13:56 |
| 1996 | Erin McChesney | Cougar's Fete | 3/4 Arabian | M | 14 | 15:38 |
| 1997 | Marcia Smith | On A High | Arabian | G | 13 | 14:32 |
| 1998 | Potato Richardson | Fille de Cailana | Arabian | M | 14 | 15:44 |
| 1999 | Rebecca Fiedler | BRR Aurber Lights | Arabian | G | 14 | 14:00 |
| 2000 | Judy Reens | Benjih+ | Arabian | G | 9 | 15:13 |
| 2001 | Marcia Smith | Saamson CC | Arabian | G | 12 | 14:48 |
| 2002 | Potato Richardson | SMR Fayette de Cameo | Arabian/Shagya | M | 7 | 15:23 |
| 2003 | Heather Reynolds | Master Motion | Arabian | G | 9 | 16:23 |
| 2004 (Tie) |
Jeremy Reynolds | CV Eli | Aarbian | G | 10 | 15:59 |
| Becky Spencer | Oritos Sonny | Arabian | G | 7 | 15:59 | |
| 2005 | Cathy Rohm Richardson | SMR Fifi d'Or | Arabian | M | 8 | 15:51 |
| 2006 | John Crandall III | Heraldic | Arabian | G | 8 | 15:08 |
| 2007 | Jeremy Reynolds | CV Eli | Arabian | G | 13 | 14:28 |
| 2008 | No ride due to wildfire | |||||
| 2009 | Sarah Engsberg | K-Zar Emmanuel | Arabian | G | 15 | 15:05 |
| 2010 | John Crandell III | Heraldic | Arabian | G | 12 | 14:59 |
| 2011 | Jeremy Reynolds | Riverwatch | Arabian | G | 7 | 10:31 (A modified Auburn-to-Auburn course was used due to weather) |
| 2012 | Garrett Ford | The Fury | Arabian | G | 13 | 14:50 |
| 2013 | Rusty Toth | Take A Break (Quake) | Arabian | G | 8 | 14:57 |
| 2014 | Heather Reynolds | French Open (Hadea) | Arabian | G | 14 | 14:17 |
| 2015 | Potato Richardson | SMR Filouette | Arabian | M | 14 | 14:50 |
| 2016 | Karen Donley | Royal Patron | Arabian | M | 14 | 14:33 |
| 2017 | Tennessee Lane | Auli Farwa (Far) | Arabian | G | 17 | 14:45 |
| 2018 | Heather Reynolds | Cayucos (Cayu) | Arabian | G | 10 | 14:45 |
| 2019 | Sanoma Blakeley | RA Ares Bay (Goober) | Arabian | G | 10 | 14:12 |
| 2020 | Ride cancelled due to Covid-19 pandemic | |||||
| 2021 | Jeremy Reynolds | Treasured Moments | Arabian | M | 12 | 14:48 |
