Stadium: Court 7 Round: 44 Ground: Hardcourt outdoor
| ITF M15 Chornomorsk | 2021/09/02 09:55 | Tommaso Compagnucci v Oleg Prihodko | 0-6,6-7 |
| ITF M15 Chornomorsk | 2021/09/01 10:10 | Grigoriy Lomakin v Tommaso Compagnucci | 6-7,6-4,2-6 |
| ITF M15 Lodz | 2021/08/19 10:00 | Tommaso Compagnucci v Soares Klier, Gilbert | 4-6,2-6 |
| ITF M15 Lodz | 2021/08/18 08:00 | Bergevi, Filip v Tommaso Compagnucci | 6-7,6-4,6-7 |
| ITF M15 Lodz | 2021/08/16 11:30 | Tommaso Compagnucci v Basing, Max | 7-5,6-1 |
| ITF M15 Vejle | 2021/07/28 07:55 | Tommaso Compagnucci v Karl Friberg | 4-6,7-5,4-6 |
| ITF M15 Vejle | 2021/07/26 11:55 | Oscar Moraing v Tommaso Compagnucci | 4-6,6-4,4-10 |
| ITF M15 Esch/Alzette | 2021/07/23 10:50 | Tommaso Compagnucci v Patrick Kypson | 3-6,5-7 |
| ITF M15 Sozopol | 2021/09/12 10:00 | Macovei, Radu Florin v Penev, Ivan | 4-6,3-6 |
| UTR Pro Tennis Series Sofia | 2021/09/01 11:00 | Samuil Konov v Penev, Ivan | 4-6,6-1,6-0 |
| UTR Pro Tennis Series Sofia | 2021/08/31 06:30 | Dimitrov, Martin v Penev, Ivan | 1-6,6-3,6-3 |
| UTR Pro Tennis Series Sofia | 2021/08/30 11:15 | Zukas, Matias v Penev, Ivan | 7-5,6-3 |
| UTR Pro Tennis Series Sofia | 2021/08/29 12:30 | Penev, Ivan v Alexandru Luca | 6-1,6-4 |
| ITF Bulgaria F1 | 2018/05/15 08:25 | Penev, Ivan v Seifert, Stefan | 4-6,2-6 |