Stadium: Court 4 Round: 26 Ground: Hardcourt outdoor
| Challenger Champaign | 2021/11/15 21:05 | Prajnesh Gunneswaran v Vasil Kirkov | 5-7,1-6 |
| 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 |
| ITF M15 Monastir | 2021/11/17 10:00 | Alexis Boureau v Gage Brymer | 6-4,7-5 |
| ITF M15 Monastir | 2021/11/13 10:00 | Gage Brymer v Dominik Boehler | 2-6,1-6 |
| ITF M15 Monastir | 2021/11/12 10:10 | Simon Beaupain v Gage Brymer | 4-6,3-6 |
| ITF M15 Monastir | 2021/11/11 12:00 | Florent Bax v Gage Brymer | 6-3,3-6,4-6 |
| ITF M15 Monastir | 2021/11/09 12:00 | Amaan Siddiqui v Gage Brymer | 0-6,0-6 |
| ITF M15 Monastir | 2021/11/03 08:30 | Robin Bertrand v Gage Brymer | 7-6,6-2 |
| ITF M25 Calabasas | 2021/10/29 22:25 | Gage Brymer v Govind Nanda | 7-6,5-7,0-6 |
| ITF M25 Calabasas | 2021/10/28 16:55 | Gage Brymer v Kyle Kang | 6-4,2-6,7-5 |