Stadium: Center Court Round: 25 Ground: Hardcourt outdoor
| Challenger - Bengaluru | 2023/02/20 05:45 | Gunneswaran, Prajnesh v Carlos Sanchez Jover | 6-4,6-3 |
| Challenger - Bengaluru | 2023/02/19 07:10 | Gunneswaran, Prajnesh v Benjamin Lock | 7-5,6-4 |
| Challenger - Chennai | 2023/02/14 06:35 | Jay Clarke v Gunneswaran, Prajnesh | 4-6,6-3,7-6 |
| Coupe Davis | 2023/02/04 09:00 | Elmer Moller v Gunneswaran, Prajnesh | 4-6,6-7 |
| ITF M25 Al Zahra | 2023/01/29 14:00 | Khumoyun Sultanov v Gunneswaran, Prajnesh | 2-6,6-7 |
| ITF M25 Al Zahra | 2023/01/28 11:00 | Gunneswaran, Prajnesh v Benjamin Hassan | 6-4,2-6,6-0 |
| ITF M25 Al Zahra | 2023/01/27 08:00 | Jakub Mensik v Gunneswaran, Prajnesh | 2-6,1-6 |
| ITF M25 Al Zahra | 2023/01/26 07:00 | Dax Donders v Gunneswaran, Prajnesh | 3-6,2-6 |
| Challenger - Chennai | 2023/02/16 07:15 | Hamad Medjedovic v James Duckworth | 2-6,6-7 |
| Challenger - Chennai | 2023/02/14 04:30 | Leo Borg v Hamad Medjedovic | 1-6,6-4,2-6 |
| Coupe Davis | 2023/02/04 16:00 | Viktor Durasovic v Hamad Medjedovic | 4-6,7-6,4-10 |
| Challenger - Tenerife | 2023/01/15 14:40 | Hamad Medjedovic v Ulises Blanch | 6-3,5-7,3-6 |
| Challenger - Oeiras | 2023/01/10 15:30 | Hamad Medjedovic v Joris De Loore | 6-7,3-6 |
| Challenger - Oeiras | 2023/01/04 11:00 | Filip Cristian Jianu v Hamad Medjedovic | 6-2,6-3 |
| Challenger - Oeiras | 2023/01/02 18:00 | Lucas Gerch v Hamad Medjedovic | 4-6,3-6 |
| Helsinki, Finland | 2022/11/13 09:00 | Hamad Medjedovic v Alibek Kachmazov | 6-4,4-6,6-7 |