Stadium: Court 5 Round: 26 Ground: Hardcourt indoor
| ITF M15 - Cancun | 2019/12/15 15:00 | Nick Chappell v Vasil Kirkov | 7-6,6-7,6-7 |
| 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 |
| ITF M15 Tallahassee | 2021/10/31 14:00 | Johannes Ingildsen v Vasil Kirkov | 6-4,1-6,2-6 |
| ITF M15 Tallahassee | 2021/10/30 13:55 | Vasil Kirkov v Henry Patten | 4-6,6-3,6-3 |
| ITF M15 Tallahassee | 2021/10/29 13:55 | Ben Shelton v Vasil Kirkov | 6-7,6-2,3-6 |
| Challenger - Champaign | 2021/11/15 21:40 | Emilio Nava v Nick Chappell | 3-6,6-7 |
| Challenger - Knoxville | 2021/11/07 19:10 | Nick Chappell v Johannus Monday | 6-4,5-7,3-6 |
| Challenger - Charlottesville | 2021/11/02 23:00 | Nick Chappell v Tung-Lin Wu | 4-6,3-6 |
| Challenger - Charlottesville | 2021/11/01 14:00 | Nick Chappell v Omni Kumar | 6-3,7-5 |
| Challenger - Charlottesville | 2021/10/31 19:40 | Nick Chappell v Gianni Ross | 6-2,6-4 |
| Challenger - Las Vegas | 2021/10/25 22:30 | Michael Mmoh v Nick Chappell | 6-2,6-1 |
| Challenger - Las Vegas | 2021/10/25 18:00 | Nick Chappell v Shintaro Mochizuki | 7-5,2-6,2-6 |
| Challenger - Las Vegas | 2021/10/24 17:00 | Nick Chappell v Roy Smith | 7-6,6-7,6-2 |