| Year | Rider | Horse | Breed | Sex | Age |
|---|---|---|---|---|---|
| 1964 | Paige Harper | Keno | Arabian | G | 6 |
| 1965 | Wendell Robie | Siri | Arabian | S | 6 |
| 1966 | Frank Moan | Barney | TB/Quarter | G | 7 |
| 1967 | Bud Dardi | Pancho | 1/2 Arabian | G | 11 |
| 1968 | Paige Harper | Raskela | Arabian | S | 7 |
| 1969 | Walter Tibbitts | Ruff Spots Banner | Appaloosa | G | 10 |
| 1970 | Suzanne Morstad | Rajah | 1/2 Arabian | G | 6 |
| 1971 | Vicki Anderson | Sheba | 3/4 Arabian | M | 9 |
| 1972 | Hal V. Hall | El Karbaj | Arabian | G | 6 |
| 1973 | Minette Rice-Edwards | Bright Hope | Anglo/Arab | M | 8 |
| 1974 | Eva Taylor | Hugo | Mule | G | 9 |
| 1975 | Wiggy Wisdom | Narabi | Arabian | G | 8 |
| 1976 | Sam Arnold | R.C. Champ | Arabian | G | 8 |
| 1977 | William Fox | Hazz | Arabian | G | 6 |
| 1978 | Hal V. Hall | El Karbaj | Arabian | G | 12 |
| 1979 | Mary Tiscornia | Royal | Arabian | G | 13 |
| 1980 | Hugh Bryson | Rajab | Arabian | G | 9 |
| 1981 | Linda Gallaher | Rajahid's Nugget | Arabian | G | 10 |
| 1982 | Jack Garnett | Ntiko Saracen | 1/2 Arabian | G | 11 |
| 1983 | Juliette Suhr | HCC Gazal | Arabian | G | 7 |
| 1984 | Juliette Suhr | HCC Gazal | Arabian | G | 8 |
| 1985 | Emmett Ross | Kachina Firewind | 3/4 Arabian | G | 10 |
| 1986 | Juliette Suhr | HCC Gazal | Arabian | G | 10 |
| 1987 | Sherode Powers | Amon Tu | Arabian | G | 7 |
| 1988 | Raymond Visco | Headhunter | Arab/Std. Brd. | G | 8 |
| 1989 | (The James Ben Ali Haggin Cup was not awarded in 1989) | ||||
| 1990 | Daniel Bunn | Harry | Arabian | G | 12 |
| 1991 | Erin McChesney | Cougar's Fete | 3/4 Arabian | M | 9 |
| 1992 | Marcia Smith | Harry | Arabian | G | 14 |
| 1993 | Cassandra Schuler | Magnet | Arabian | G | 7 |
| 1994 | Cassandra Schuler | Magnet | Arabian | G | 8 |
| 1995 | Hugh Helm | Petruska | Arabian | M | 9 |
| 1996 | Erin McChesney | Cougar's Fete | 3/4 Arabian | M | 14 |
| 1997 | Ona Lawrence | Dandy McCoy | Arabian | G | 16 |
| 1998 | Sandy Brown | Ruby | Mule | M | 8 |
| 1999 | Heather Bergantz | Crystal's Charm | Arabian | G | 7 |
| 2000 | Elise Geske | Ravi Das | Arabian | G | 10 |
| 2001 | Cathy Rohm | Fayette de Cameo | Shagya Arab | M | 6 |
| 2002 | Hal V. Hall | Bogus Thunder | Arabian | G | 9 |
| 2003 | Heather Bergantz Reynolds | Master Motion | Arabian | G | 9 |
| 2004 | Jeremy Reynolds | CV Eli | Arabian | G | 10 |
| 2005 | Michele Roush | Diamond Sunn Bask (Cayenne) | Arabian | G | 9 |
| 2006 | John Crandall | Heraldic | Arabian | G | 8 |
| 2007 | John Crandall | HH Saba Shams | Arabian | G | 8 |
| 2008 | No ride due to wildfire | ||||
| 2009 | Melissa Ribley | LD Monique | Arabian | M | 13 |
| 2010 | Garrett Ford | The Fury | Arabian | G | 8 |
| 2011 | Jeremy Reynolds | Riverwatch | Arabian | G | 7 |
| 2012 | Rusty Toth | Farrabba (Stoner) | Arabian | G | 11 |
| 2013 | Suzanne Hedgecock | LZP Julicslastchance (Julio) | Arabian | G | 12 |
| 2014 | Barrak Blakeley | MCM Last Dance | Arabian | G | 17 |
| 2015 | Jenni Smith | Auli Farwa | Arabian | G | 15 |
| 2016 | Lisa Ford | GE Cyclone | Arabian | G | 16 |
| 2017 | Jeremy Reynolds | Treasured Moments | Arabian | M | 7 |
| 2018 | Mykayla Corgnell | MM Cody | Mustang | G | 10 |
| 2019 | Lindsay Fisher | Monk | Arabian | G | 17 |
| 2020 | Ride cancelled due to Covid-19 pandemic | ||||
| 2021 | Jeanette (Jay) Mero, DVM | Ozark Kaolena SWA (Lena) | Arabian | M | 9 |
