Stadium: Court 1 Round: 25 Ground: Clay
| Challenger Columbus | 2022/01/23 17:50 | Yosuke Watanuki v Preston Stearns | 6-3,6-3 |
| UTR Pro Tennis Series Florida | 2021/09/12 15:00 | Preston Stearns v Patrick Daciek | 1-6,4-5 |
| UTR Pro Tennis Series Florida | 2021/09/11 16:30 | Preston Stearns v Jacob Perkins | 3-6,6-4,5-3 |
| UTR Pro Tennis Series Florida | 2021/09/09 13:30 | Preston Stearns v Jonah Braswell | 4-6,0-1 |
| UTR Pro Tennis Series Florida | 2021/09/08 13:30 | Preston Stearns v Matthew Segura | 6-4,7-6 |
| UTR Pro Tennis Series Florida | 2021/09/07 16:30 | Preston Stearns v Victor Sklenka | 4-6,7-5,4-6 |
| UTR Pro Tennis Series Florida | 2021/09/06 21:00 | Preston Stearns v Noureldin Adam | 2-6,6-4,2-6 |
| Challenger Puerto Vallarta | 2021/11/21 16:00 | Vasil Kirkov v Ivar Jose Aramburu Contreras | 6-1,6-2 |
| Challenger Champaign | 2021/11/19 18:25 | Vasil Kirkov v Jeffrey John Wolf | 3-6,2-6 |
| Challenger Champaign | 2021/11/17 16:00 | Vasil Kirkov v Nick Chappell | 6-2,6-3 |
| Challenger Champaign | 2021/11/15 21:05 | Prajnesh Gunneswaran v Vasil Kirkov | 5-7,1-6 |
| ITF M15 Ithaca | 2021/11/06 13:55 | Luke Johnson v Vasil Kirkov | 6-1,6-1 |
| ITF M15 Ithaca | 2021/11/05 13:50 | Evan Bynoe v Vasil Kirkov | 1-6,1-6 |
| ITF M15 Ithaca | 2021/11/04 16:45 | Colin Sinclair v Vasil Kirkov | 3-6,4-6 |
| ITF M15 Ithaca | 2021/11/03 18:35 | John McNally v Vasil Kirkov | 7-6,2-6,1-6 |