Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| Challenger Knoxville | 2021/11/10 23:45 | Sock, Jack v Gunneswaran, Prajnesh | 6-3,7-6 |
| Challenger Knoxville | 2021/11/08 20:00 | Gunneswaran, Prajnesh v Torpegaard, Mikael | 6-2,7-6 |
| Challenger Charlottesville | 2021/11/05 16:00 | Schnur, Brayden v Gunneswaran, Prajnesh | 7-5,6-3 |
| Challenger Charlottesville | 2021/11/03 21:00 | Inaki Montes-De La Torre v Gunneswaran, Prajnesh | 1-6,5-7 |
| Challenger Charlottesville | 2021/11/01 20:50 | Gunneswaran, Prajnesh v Taro Daniel | 6-7,7-6,6-2 |
| Challenger Columbus | 2021/09/23 15:00 | Gunneswaran, Prajnesh v Torpegaard, Mikael | 1-6,4-6 |
| Challenger Columbus | 2021/09/21 22:35 | Gunneswaran, Prajnesh v Aleksandar Kovacevic | 3-6,6-3,7-5 |
| Coupe Davis | 2021/09/18 12:55 | Niklas-Salminen, Patrick v Gunneswaran, Prajnesh | 3-6,5-7 |
| ITF M15 Ithaca | 2021/11/06 13:55 | Johnson, Luke v Kirkov, Vasil | 6-1,6-1 |
| ITF M15 Ithaca | 2021/11/05 13:50 | Evan Bynoe v Kirkov, Vasil | 1-6,1-6 |
| ITF M15 Ithaca | 2021/11/04 16:45 | Colin Sinclair v Kirkov, Vasil | 3-6,4-6 |
| ITF M15 Ithaca | 2021/11/03 18:35 | Mcnally, John v Kirkov, Vasil | 7-6,2-6,1-6 |
| ITF M15 Tallahassee | 2021/10/31 14:00 | Johannes Ingildsen v Kirkov, Vasil | 6-4,1-6,2-6 |
| ITF M15 Tallahassee | 2021/10/30 13:55 | Kirkov, Vasil v Patten, Henry | 4-6,6-3,6-3 |
| ITF M15 Tallahassee | 2021/10/29 13:55 | Ben Shelton v Kirkov, Vasil | 6-7,6-2,3-6 |
| ITF M15 Tallahassee | 2021/10/28 15:50 | Mcnally, John v Kirkov, Vasil | 4-6,2-6 |