Stadium: Court 5 Round: 44 Ground: Hardcourt outdoor
| ITF M15 Sozopol | 2021/10/10 10:30 | Tommaso Compagnucci v S Mert Ozdemir | 6-2,7-5 |
| ITF M15 Vyshkovo | 2021/09/25 08:00 | Nedelko, Ivan v Tommaso Compagnucci | 6-2,6-7,6-4 |
| ITF M15 Vyshkovo | 2021/09/24 10:00 | Tommaso Compagnucci v Aleksandr Braynin | 3-6,7-5,6-1 |
| ITF M15 Vyshkovo | 2021/09/21 07:00 | Bondarevskiy, Yan v Tommaso Compagnucci | 2-6,7-6,5-7 |
| ITF M15 Sozopol | 2021/09/17 06:55 | Martin Krumich v Tommaso Compagnucci | 6-2,6-4 |
| ITF M15 Sozopol | 2021/09/16 10:05 | Tommaso Compagnucci v Petr Nesterov | 6-2,6-0 |
| ITF M15 Sozopol | 2021/09/15 10:00 | Tommaso Compagnucci v Sadaoui, Mehdi | 6-3,6-1 |
| ITF M15 Sozopol | 2021/09/14 07:00 | Tommaso Compagnucci v Caspar Schuetze | 6-1,6-2 |
| ITF M15 Sozopol | 2021/10/10 10:30 | Dimitrov, Martin v Popeanga, Dragos Petre | 6-3,6-4 |
| ITF M15 Sozopol | 2021/10/06 09:35 | Dimitrov, Martin v Cozbinov, Alexander | 1-6,3-6 |
| ITF M15 Sozopol | 2021/10/05 06:30 | Stoica, Vlad v Dimitrov, Martin | 1-6,2-6 |
| ITF M15 Sozopol | 2021/10/04 07:00 | Suleyman Deniz Gursoy v Dimitrov, Martin | 2-6,1-6 |
| ITF M15 Sozopol | 2021/09/15 07:00 | Dimitrov, Martin v Manda, Calin | 4-6,4-6 |
| ITF M15 Sozopol | 2021/09/13 07:00 | Dimitrov, Martin v Shandarov, Radoslav | 6-7,6-2,14-12 |
| UTR Pro Tennis Series Sofia | 2021/09/02 07:00 | Dimitrov, Martin v Dian Nedev | 3-6,3-5 |
| UTR Pro Tennis Series Sofia | 2021/09/01 11:00 | Dimitrov, Martin v Zukas, Matias | 0-6,2-5 |