Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| 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 |
| Davis Cup | 2021/09/17 14:50 | Otto Virtanen v Prajnesh Gunneswaran | 6-3,7-6 |
| Challenger Saint-Tropez | 2021/08/30 12:25 | Prajnesh Gunneswaran v Hugo Grenier | 5-7,3-6 |
| US Open | 2021/08/26 18:20 | Christopher Eubanks v Prajnesh Gunneswaran | 6-3,6-4 |
| US Open | 2021/08/25 15:00 | Brayden Schnur v Prajnesh Gunneswaran | 4-6,6-7 |
| ATP Washington | 2021/08/03 18:00 | Prajnesh Gunneswaran v Emil Ruusuvuori | 6-2,1-6,1-6 |
| 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 |
| ITF M15 Tallahassee | 2021/10/27 18:00 | Liam Draxl v Vasil Kirkov | 3-6,3-6 |
| ITF M25 Prague | 2021/10/07 13:00 | Timo Stodder v Vasil Kirkov | 6-2,6-1 |
| ITF M25 Prague | 2021/10/06 07:55 | Vasil Kirkov v Adam Januska | 6-0,6-0 |
| ITF M25 Falun | 2021/10/01 14:30 | Vasil Kirkov v Shintaro Imai | 2-6,5-7 |