Estádio: Center Court Round: 14 Ground: Clay
| Challenger - Porto | 2021/07/01 10:00 | Steven Diez v Prajnesh Gunneswaran | 6-3,1-6,6-4 |
| Challenger - Porto | 2021/06/29 16:10 | Mathias Bourgue v Prajnesh Gunneswaran | 2-6,6-3,1-6 |
| Wimbledon | 2021/06/22 13:30 | Arthur Fery v Prajnesh Gunneswaran | 6-1,7-6 |
| Open de França | 2021/05/25 08:30 | Oscar Otte v Prajnesh Gunneswaran | 6-2,6-2 |
| ATP - Genebra | 2021/05/16 08:30 | Prajnesh Gunneswaran v Mackenzie McDonald | 3-6,6-3,3-6 |
| Challenger - Heilbronn | 2021/05/10 15:40 | Alessandro Giannessi v Prajnesh Gunneswaran | 7-6,6-1 |
| ATP - Munique | 2021/04/24 12:15 | Prajnesh Gunneswaran v Dennis Novak | 4-6,6-3,5-7 |
| Challenger - Tallahassee | 2021/04/19 17:00 | Prajnesh Gunneswaran v Pedro Sakamoto | 2-6,6-2,4-6 |
| ITF - M25 Alkmaar | 2021/06/22 08:55 | Gijs Brouwer v Benjamin Hassan | 1-6,7-6,7-5 |
| Challenger - Almaty | 2021/06/14 06:10 | Vitaliy Sachko v Benjamin Hassan | 4-6,6-3,6-1 |
| Challenger - Almaty - Qualificação | 2021/06/13 10:05 | Tsung-Hua Yang v Benjamin Hassan | 1-6,3-6 |
| Challenger - Almaty | 2021/06/07 04:00 | Evan Furness v Benjamin Hassan | 6-3,3-6,6-4 |
| Challenger - Almaty | 2021/06/06 06:45 | Benjamin Hassan v Ivan Nedelko | 6-2,6-2 |
| ITF - M15 Antália | 2021/05/27 07:25 | Mariano Navone v Benjamin Hassan | 6-2,5-7,6-3 |
| ITF - M15 Antália | 2021/05/25 12:45 | Gokberk Saritas v Benjamin Hassan | 1-6,0-6 |
| ITF - M15 Antália | 2021/05/22 07:30 | Nick Hardt v Benjamin Hassan | 6-3,6-1 |