Stadium: Court 5 Round: 44 Ground: Clay
| UTR Pro Tennis Series Copenhagen | 2022/04/30 10:30 | Dimitrov, Martin v Milushev, Plamen | 4-6,7-5,5-2 |
| Plovdiv, Singles Qualifying M-ITF-BUL-03A | 2019/06/04 06:30 | Dimitrov, Martin v Milushev, Plamen | 6-0,5-7,9-11 |
| UTR Pro Tennis Series Copenhagen | 2022/04/30 10:30 | Dimitrov, Martin v Milushev, Plamen | 4-6,7-5,5-2 |
| UTR Pro Tennis Series Copenhagen | 2022/04/28 07:30 | Dimitrov, Martin v John Walentowicz | 4-6,6-3,5-1 |
| UTR Pro Tennis Series Copenhagen | 2022/04/27 06:00 | Dimitrov, Martin v Korsgaard, Henrik Heise | 2-6,7-6,3-6 |
| UTR Pro Tennis Series Copenhagen | 2022/04/26 09:00 | Dimitrov, Martin v Maciej Rajski | 0-6,4-6 |
| UTR Pro Tennis Series Copenhagen | 2022/04/25 07:30 | Dimitrov, Martin v Ruzgas, Marius | 4-6,7-6,5-4 |
| UTR Pro Tennis Series Dobrich | 2022/02/27 07:23 | Petr Nesterov v Dimitrov, Martin | 6-3,4-6,7-5 |
| UTR Pro Tennis Series Dobrich | 2022/02/26 09:29 | Dimitrov, Martin v Gabriel Donev | 6-4,1-4 |
| UTR Pro Tennis Series Dobrich | 2022/02/25 09:00 | Penev, Ivan v Dimitrov, Martin | 7-5,6-1 |
| UTR Pro Tennis Series Copenhagen | 2022/04/30 10:30 | Dimitrov, Martin v Milushev, Plamen | 4-6,7-5,5-2 |
| UTR Pro Tennis Series Copenhagen | 2022/04/28 06:00 | Milushev, Plamen v Ganchev, Alex | 4-6,6-2,6-3 |
| UTR Pro Tennis Series Copenhagen | 2022/04/27 09:00 | Milushev, Plamen v Ivanov, Simon Anthony | 3-6,7-6,1-6 |
| UTR Pro Tennis Series Copenhagen | 2022/04/26 06:00 | Milushev, Plamen v Marcelo Zormann | 4-6,6-6 |
| UTR Pro Tennis Series Copenhagen | 2022/04/25 10:55 | Milushev, Plamen v Christian Heaney-Secord | 1-6,3-6 |
| UTR Pro Tennis Series Barcelona | 2022/03/31 14:08 | Penev, Ivan v Milushev, Plamen | 6-2,1-0 |
| UTR Pro Tennis Series Barcelona | 2022/03/30 09:30 | Robert, Quentin v Milushev, Plamen | 6-2,6-2 |
| UTR Pro Tennis Series Barcelona | 2022/03/29 12:00 | Vladimir Popov v Milushev, Plamen | 3-6,1-6 |