Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| French Open | 2021/05/25 08:30 | Oscar Otte v Prajnesh Gunneswaran | 6-2,6-2 |
| ATP Geneva | 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 Munich | 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 |
| Challenger Orlando | 2021/04/15 16:30 | Prajnesh Gunneswaran v Jack Sock | 3-6,4-6 |
| Challenger Orlando | 2021/04/13 16:20 | Prajnesh Gunneswaran v Matthew Ebden | 6-4,6-1 |
| ATP Dubai | 2021/03/13 07:00 | Yuki Bhambri v Prajnesh Gunneswaran | 6-1,6-4 |
| ITF M25 Tulsa | 2021/06/15 14:00 | Vasil Kirkov v Michael Shabaz | 3-6,6-1,7-10 |
| ITF M25 Tulsa | 2021/06/14 15:00 | Vasil Kirkov v Errol Smith | 6-4,6-4 |
| ITF M15 Heraklion | 2020/11/26 07:30 | Henry Patten v Vasil Kirkov | 6-4,6-1 |
| ITF M15 Heraklion | 2020/11/25 09:55 | Vasil Kirkov v Lucas Catarina | 2-6,6-2,6-4 |
| ITF M15 Heraklion | 2020/11/18 12:15 | Vasil Kirkov v Sho Shimabukuro | 2-6,6-3,4-6 |
| ITF M15 Heraklion | 2020/11/17 07:30 | Vasil Kirkov v Billy Harris | 4-6,6-0,10-7 |
| ITF M15 Heraklion | 2020/11/16 07:30 | Vasil Kirkov v Gianmarco Ferrari | 4-6,6-2,10-2 |
| ITF M15 Heraklion | 2020/11/15 08:00 | Vasil Kirkov v Cezar Cretu | 6-4,6-3 |