THEODORA A. RANDOLPH FIELD HUNTER CHAMPIONSHIP WINNERS
| YEAR | HORSE | OWNER | RIDER | HUNT |
| 1984 | To Be Identified | Mrs. A. C. Randolph | To Be Identified | Piedmont Fox Hounds |
| 1985 | Newton Thomas | Mrs. William Abel-Smith | Victoria Abel-Smith | Piedmont Fox Hounds |
| 1986 | Beacon Rock | Mrs. Joan Batterton | Joan Batterton | Blue Ridge Hunt |
| 1987 | Racetrack Harry | Mrs. Mary H. D. Swift | Mary Swift | Piedmont Fox Hounds |
| 1988 | Mitey Toddy | Mrs. Gay Estin | Gay Estin | Orange County Hunt |
| 1989 | Sundance | Mrs. William Haggin Perry | Woods Winants | Middleburg Hunt |
| 1990 | Arm a Native | Mrs. Theodora A. Randolph | Joanne Hammond | Piedmont Fox Hounds |
| 1991 | Brownstone Bandit | Dr. John Earle Cross | John Cross | Blue Ridge Hunt |
| 1992 | Candy Man | Mrs. Joan Batterton | Joan Batterton | Blue Ridge Hunt |
| 1993 | Henry | Mr. Peter Hitchen | Peter Hitchen | Potomac Hunt |
| 1994 | Rey De France | Mr. James H. Whitner | Cricket Bedford | Piedmont Fox Hounds |
| 1995 | Catch a Dream | Mrs. Donna Eicher | Donna Eicher | Keswick Hunt |
| 1996 | Lord Hugh | Kathleen O'Keefe | Kathleen O'Keefe | Loudoun Hunt West |
| 1997 | Get Smart | Richard Laimbeer | Richard Laimbeer | Warrenton Hunt |
| 1998 | Serene Citadel | Carolyn Chapman | Carolyn Chapman | Farmington Hunt |
| 1999 | Nell's Magic | Mary Southwell Hutchison | Mary Southwell Hutchison | Orange County Hunt |
| 2000 | Big Boy | Tivoli Farm | William S. Coleman | Farmington Hunt |
| 2001 | Doctor No | Kathleen M. B. Berger | Kathleen M. B. Berger | Blue Ridge Hunt |
| 2002 | Laird Ivor | Mr. Paul Briede | Loretta Briede | Blue Ridge Hunt |
| 2003 | Bay | Hart Farm | Susie Hart | Loudoun Hunt West |
| 2004 | Aladdin | Hart Farm | Candace Madigan | Loudoun Hunt West |
| 2005 | Penn Park | Ms. Susan Deal | Susan Deal | Rappahannock Hunt |
| 2006 | Gol Lee | Kathleen O'Keefe | Kathleen O'Keefe | Casanova Hunt |
| 2007 | Morning Pleasure | Mrs. Paul Fout | Eve Fout | Orange County Hunt |
| 2008 | Dennis the Menace | Susan McHugh | Susan McHugh | Aiken Hounds |
| 2009 | Not Held | |||
| 2010 | Another Day | Emily Day & Ms. Whitney Hagan | Emily Day | Blue Ridge Hunt |
| 2011 | Dudley | Hart Farm | Kathleen O'Keefe | Casanova Hunt |
| 2012 | Gold For Glory | Mr. Shelby Bonnie | Elizabeth Green | Piedmont Fox Hounds |
| 2013 | Greyland Woods | Ms. Karen Martz | Teresa Croce | Loudoun Hunt West |
| 2014 | Stretch | Mrs. Laurie Ambrose | Laurie Ambrose | Piedmont Fox Hounds |
| 2015 | Ace | Tivoli Farm | Will Coleman | Keswick Hunt |
| 2015 | Toto | Scott & Christie Fitzsimmons | Tom Mansmann | Piedmont Fox Hounds |
| 2016 | Battalion | Mrs. Cameron Sadler, MFH | Cameron Sadler | Moore County Hounds |
| 2016 | Greyland Woods | Ms. Karen Martz | Teresa Croce | Middleburg Hunt |
| 2017 | Rita | Mr. & Mrs. Frank Becker | Mackenzie Taylor | Goshen Hunt |
| 2018 | Socrates | John Wittenborn | John Wittenborn | Smithtown Hunt |
| 2019 | Skye's Limit | Kate Gilhool | Kate Gilhool | Elkridge-Harford Hunt |
|
2021 |
Gabrina Von Schweetz | Lindsey Williamson | Lindsey Williamson |
Thornton Hill Hounds |
| 2022 |
Forever Bernardini |
Mary Chilton Crane | Mary Chilton Crane |
Norfolk Hunt |
Dr. Matthew Page Mackay-Smith Award for Highest Placing Thoroughbred
| YEAR | HORSE | OWNER | RIDER | HUNT |
| 2019 | Thunderville | Linden Ryan, Jocelyn Coles, Ross Salter | Linden Ryan | Blue Ridge Hunt |
| 2021 | Forever Bernardini | Mary Chilton Crane | Mary Chilton Crane | Norfolk Hunt |
| 2022 |
Forever Bernardini |
Mary Chilton Crane | Mary Chilton Crane | Norfolk Hunt |