Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| Challenger - Knoxville | 2021/11/10 23:45 | Jack Sock v Prajnesh Gunneswaran | 6-3,7-6 |
| Challenger - Knoxville | 2021/11/08 20:00 | Prajnesh Gunneswaran v Mikael Torpegaard | 6-2,7-6 |
| Challenger - Charlottesville | 2021/11/05 16:00 | Brayden Schnur v Prajnesh Gunneswaran | 7-5,6-3 |
| Challenger - Charlottesville | 2021/11/03 21:00 | Inaki Montes-De La Torre v Prajnesh Gunneswaran | 1-6,5-7 |
| Challenger - Charlottesville | 2021/11/01 20:50 | Prajnesh Gunneswaran v Taro Daniel | 6-7,7-6,6-2 |
| Challenger - Columbus | 2021/09/23 15:00 | Prajnesh Gunneswaran v Mikael Torpegaard | 1-6,4-6 |
| Challenger - Columbus | 2021/09/21 22:35 | Prajnesh Gunneswaran v Aleksandar Kovacevic | 3-6,6-3,7-5 |
| Davis Cup | 2021/09/18 12:55 | Patrik Niklas-Salminen v Prajnesh Gunneswaran | 3-6,5-7 |
| 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 |
| ITF M15 Tallahassee | 2021/10/28 15:50 | John McNally v Vasil Kirkov | 4-6,2-6 |