Winners of both the Tevis Cup and the Haggin Cup in the same year: 1991 and 1996 Erin McChesney and Cougar's Fete; 2003 Heather Bergantz Reynolds and Master Motion; 2011 Jeremy Reynolds and Riverwatch
| Year | Tevis Cup - Best Performance | Haggin Cup - Superior Condition |
|---|---|---|
| 1955 | Wendell Robie | |
| 1956 | Wendell Robie | |
| 1957 | Wendell Robie | |
| 1958 | Wendell Robie | |
| 1959 | Nick Mansfield First Award of Tevis Cup |
|
| 1960 | Ernie Sanchez | |
| 1961 | Drucilla Barner | |
| 1962 | Paige Harper | |
| 1963 | Pat Fitzgerald | |
| 1964 | Neil Hutton | Paige Harper - First Award of Haggin Cup |
| 1965 | Ed Johnson | Wendell Robie |
| 1966 | Bud Dardi | Frank Moan |
| 1967 | Ed Johnson | Bud Dardi |
| 1968 | Bud Dardi | Paige Harper |
| 1969 | Marion Robie Arnold | Walter Tibbitts |
| 1970 | Donna Fitzgerald | Suzanne Morstad |
| 1971 | Donna Fitzgerald | Vicki Anderson |
| 1972 | Donna Fitzgerald | Hal V. Hall |
| 1973 | Donna Fitzgerald | Minette Rice-Edwards |
| 1974 | Hal V. Hall | Eva Taylor |
| 1975 | Donna Fitzgerald | Wiggy Wisdom |
| 1976 | Donna Fitzgerald and Sam Arnold (Tie Finish) |
Sam Arnold |
| 1977 | Hal V. Hall | William Fox |
| 1978 | Kathie Perry | Hal V. Hall |
| 1979 | Boyd Zontelli | Mary Tiscornia |
| 1980 | Loreley Stewart | Hugh Bryson |
| 1981 | Boyd Zontelli | Linda Gallagher Bentham |
| 1982 | Marjorie Pryor | Jack Garnett |
| 1983 | Marjorie Pryor | Julie Suhr |
| 1984 | Becky Hart | Julie Suhr |
| 1985 | Boyd Zontelli | Emmett Ross |
| 1986 | Loreley Stewart | Julie Suhr |
| 1987 | Kathy Ray | Sherode Powers |
| 1988 | Becky Hart | Raymond Visco |
| 1989 | Lari Shea | not awarded |
| 1990 | Hal V. Hall | Daniel Bunn |
| 1991 | Erin McChesney | Erin McChesney |
| 1992 | Marcia Smith, DVM and Shellie Hatfield (Tie Finish) |
Marcia Smith, DVM |
| 1993 | Chris Knoch | Cassandra Schuler, DVM |
| 1994 | Chris Knoch | Cassandra Schuler, DVM |
| 1995 | Matthew Mackay-Smith | Hugh Helm |
| 1996 | Erin McChesney | Erin McChesney |
| 1997 | Marcia Smith, DVM | Ona Lawrence |
| 1998 | Potato Richardson | Sandy Brown |
| 1999 | Rebecca S. Fiedler | Heather Bergantz |
| 2000 | Judy Reens | Elise Geske |
| 2001 | Marcia Smith, DVM | Cathy Rohm |
| 2002 | Potato Richardson | Hal V. Hall |
| 2003 | Heather Bergantz Reynolds | Heather Bergantz Reynolds |
| 2004 | Jeremy Reynolds and Becky Spencer (Tie Finish) |
Jeremy Reynolds |
| 2005 | Cathy Rohm Richardson | Michele Roush |
| 2006 | John Crandall III | John Crandall III |
| 2007 | Jeremy Reynolds | John Crandall III |
| 2008 | No Ride Due To Fire | |
| 2009 | Sarah Engsberg | Melissa Ribley |
| 2010 | John Crandall III | Garrett Ford |
| 2011 | Jeremy Reynolds | Jeremy Reynolds |
| 2012 | Garrett Ford | Rusty Toth |
| 2013 | Rusty Toth | Suzanne Hedgecock |
| 2014 | Heather Reynolds | Barrak Blakeley |
| 2015 | Potato Richardson | Jenni Smith |
| 2016 | Karen Donley | Lisa Ford |
| 2017 | Tennessee Lane | Jeremy Reynolds |
| 2018 | Heather Reynolds | Mykayla Corgnell |
| 2019 | Sanoma Blakeley | Lindsay Graham Fisher, DVM |
| 2020 | Ride cancelled due to Covid-19 Pandemic | |
| 2021 | Jeremy Reynolds | Jeanette (Jay) Mero, DVM |
