Stadium: Court 5 Round: 44 Ground: Clay
| ITF M25 - Pazardzhik | 2023/10/02 07:30 | Razvan Baiant v Plamen Milushev | 4-6,6-4,5-10 |
| ITF M25 - Pazardzhik | 2023/09/27 10:55 | Hynek Barton v Plamen Milushev | 6-3,6-3 |
| ITF M25 - Pazardzhik | 2023/09/25 12:00 | Plamen Milushev v Andrea Meduri | 1-6,7-6,10-7 |
| ITF M25 - Pazardzhik | 2023/09/24 07:00 | Razvan Baiant v Plamen Milushev | 6-4,1-6,3-10 |
| ITF M15 - Sofia | 2023/07/02 06:30 | Plamen Milushev v Pierre Yves Bailly | 6-7,2-6 |
| ITF M15 - Sofia | 2022/07/03 09:00 | Martin Dimitrov v Plamen Milushev | 7-6,6-3 |
| UTR Pro Tennis Series - Köpenhamn | 2022/04/30 10:30 | Martin Dimitrov v Plamen Milushev | 4-6,7-5,5-2 |
| UTR Pro Tennis Series - Köpenhamn | 2022/04/28 06:00 | Plamen Milushev v Alex Ganchev | 4-6,6-2,6-3 |
| ITF M25 - Pazardzhik | 2023/10/02 07:30 | Anthony Shumsky v Maxwell Benson | 2-6,3-6 |
| ITF M25 - Pazardzhik | 2023/09/27 12:35 | Nikola Kolyachev v Maxwell Benson | 6-4,7-6 |
| ITF M25 - Pazardzhik | 2023/09/25 13:55 | Maxwell Benson v Felipe Mikkelsen | 7-6,6-4 |
| ITF M25 - Pazardzhik | 2023/09/25 07:00 | Vojtech Vlkovsky v Maxwell Benson | 3-6,0-6 |
| ITF M25 - Pardubice | 2023/09/18 10:30 | Tom Schonenberg v Maxwell Benson | 6-1,6-2 |
| ITF M25 - Pardubice | 2023/09/17 12:00 | Josef Vagner v Maxwell Benson | 4-6,2-6 |
| ITF M15 - Satu Mare | 2023/09/12 07:00 | Juan Cruz Martin Manzano v Maxwell Benson | 7-6,6-3 |
| ITF M15 - Satu Mare | 2023/09/11 07:00 | Botond Kisantal v Maxwell Benson | 4-6,0-6 |