Stadium: Court 2 Round: 44 Ground: Clay
| ITF M15 Sofia | 2022/07/03 09:00 | Martin Dimitrov v Plamen Milushev | 7-6,6-3 |
| UTR Pro Tennis Series Copenhagen | 2022/04/30 10:30 | Martin Dimitrov v Plamen Milushev | 4-6,7-5,5-2 |
| UTR Pro Tennis Series Copenhagen | 2022/04/28 06:00 | Plamen Milushev v Alex Ganchev | 4-6,6-2,6-3 |
| UTR Pro Tennis Series Copenhagen | 2022/04/27 09:00 | Plamen Milushev v Simon A Ivanov | 3-6,7-6,1-6 |
| UTR Pro Tennis Series Copenhagen | 2022/04/26 06:00 | Plamen Milushev v Marcelo Zormann | 4-6,6-6 |
| UTR Pro Tennis Series Copenhagen | 2022/04/25 10:55 | Plamen Milushev v Christian Heaney-Secord | 1-6,3-6 |
| UTR Pro Tennis Series Barcelona | 2022/03/31 14:08 | Ivan Penev v Plamen Milushev | 6-2,1-0 |
| UTR Pro Tennis Series Barcelona | 2022/03/30 09:30 | Quentin Robert v Plamen Milushev | 6-2,6-2 |
| ITF M15 Monastir | 2021/11/14 08:30 | Pierre Yves Bailly v Dominik Boehler | 4-6,7-6,6-2 |
| ITF M15 Monastir | 2021/11/13 10:30 | Gauthier Onclin v Pierre Yves Bailly | 1-6,6-7 |
| ITF M15 Monastir | 2021/11/11 08:00 | Guy Den Ouden v Pierre Yves Bailly | 3-6,6-7 |
| ITF M15 Monastir | 2021/11/03 08:30 | Pierre Yves Bailly v Alexis Boureau | 1-6,4-6 |
| ITF M15 Monastir | 2021/10/12 10:50 | Pierre Yves Bailly v Raphael Collignon | 6-4,5-7,1-6 |
| ITF M15 Monastir | 2021/10/07 13:35 | Skander Mansouri v Pierre Yves Bailly | 6-2,6-2 |
| ITF M15 Monastir | 2021/10/05 08:25 | Sascha Gueymard Wayenburg v Pierre Yves Bailly | 2-6,1-6 |
| ITF M15 Monastir | 2021/09/28 09:00 | Pierre Yves Bailly v Niki Kaliyanda Poonacha | 3-6,5-7 |