Stadium: Court 5 Round: 44 Ground: Hardcourt outdoor
| ITF M15 Sozopol | 2021/10/04 07:00 | Yann Wojcik v Ivan Penev | 3-6,7-5,10-2 |
| ITF M15 Sozopol | 2021/09/13 10:30 | Tommaso Compagnucci v Ivan Penev | 6-2,6-3 |
| ITF M15 Sozopol | 2021/09/12 10:00 | Radu F Macovei v Ivan Penev | 4-6,3-6 |
| UTR Pro Tennis Series Sofia | 2021/09/01 11:00 | Samuil Konov v Ivan Penev | 4-6,6-1,6-0 |
| UTR Pro Tennis Series Sofia | 2021/08/31 06:30 | Martin Dimitrov v Ivan Penev | 1-6,6-3,6-3 |
| UTR Pro Tennis Series Sofia | 2021/08/30 11:15 | Matias Zukas v Ivan Penev | 7-5,6-3 |
| UTR Pro Tennis Series Sofia | 2021/08/29 12:30 | Ivan Penev v Alexandru Luca | 6-1,6-4 |
| ITF Bulgaria F1 | 2018/05/15 08:25 | Ivan Penev v Stefan Seifert | 4-6,2-6 |
| ITF M15 Sozopol | 2021/10/03 07:00 | Yann Wojcik v Gianluca Coloma-Heck | 6-1,7-5 |
| ITF M15 Monastir | 2021/08/22 10:00 | Mohamed Amin Oueslati v Gianluca Coloma-Heck | 3-6,6-4,10-5 |
| ITF M15 Monastir | 2021/08/15 07:30 | Gianluca Coloma-Heck v Syed Mohd Agil Syed Naguib | 4-6,2-6 |
| ITF M25 Jablonec Nad Nisou | 2021/05/18 07:30 | Robin Stanek v Gianluca Coloma-Heck | 6-1,6-1 |
| ITF M25 Jablonec Nad Nisou | 2021/05/17 07:30 | Vojtech Mares v Gianluca Coloma-Heck | 6-2,4-6,4-10 |
| ITF M25 Jablonec Nad Nisou | 2021/05/16 07:30 | Jakub Beran v Gianluca Coloma-Heck | 6-4,6-7,5-10 |
| ITF M15 Monastir | 2021/03/07 10:30 | Gianluca Coloma-Heck v Alexander Kotzen | 0-6,1-6 |
| ITF M15 Antalya | 2020/12/06 07:00 | Mert Alkaya v Gianluca Coloma-Heck | 2-6,6-2,10-4 |