Stadium: Court 7 Round: 26 Ground: Hardcourt outdoor
| ITF - M15 Sozopol | 2022/10/05 07:00 | Simeon Terziev v Iliyan Radulov | 4-6,3-6 |
| ITF - M15 Sofia | 2022/07/05 08:40 | Iliyan Radulov v Rrezart Cungu | 4-6,6-4,3-6 |
| UTR Pro Tennis Series - Pazardzhik | 2021/07/17 12:00 | Iliyan Radulov v Plamen Milushev | 6-3,1-6,2-6 |
| UTR Pro Tennis Series - Pazardzhik | 2021/07/16 07:30 | Iliyan Radulov v Ilya Snitari | 3-6,2-6 |
| UTR Pro Tennis Series - Pazardzhik | 2021/07/15 10:30 | Iliyan Radulov v Denislav Prodanov | 2-6,2-6 |
| UTR Pro Tennis Series - Pazardzhik | 2021/07/14 06:00 | Dian Nedev v Iliyan Radulov | 7-5,6-1 |
| UTR Pro Tennis Series - Pazardzhik | 2021/07/13 09:00 | Aristotelis Thanos v Iliyan Radulov | 4-2 |
| ITF - M15 Sozopol | 2022/10/05 08:25 | Olaf Pieczkowski v Riccardo Balzerani | 7-5,6-3 |
| Cupa Davis | 2022/09/17 12:15 | Olaf Pieczkowski v Lucky Candra Kurniawan | 6-4,6-2 |
| Cupa Davis | 2022/09/16 14:30 | Olaf Pieczkowski v Fitriadi M Rifqi | 7-5,6-0 |
| ITF - M25 Poznan | 2022/08/27 11:45 | Valerio Aboian v Olaf Pieczkowski | 6-2,6-3 |
| ITF - M25 Poznan | 2022/08/26 10:30 | Olaf Pieczkowski v Georgii Kravchenko | 6-4,6-3 |
| ITF - M25 Poznan | 2022/08/25 10:25 | Tomasz Berkieta v Olaf Pieczkowski | 3-6,2-6 |
| ITF - M25 Poznan | 2022/08/24 10:00 | Olaf Pieczkowski v Michal Matuszewski | 6-1,6-1 |
| Challenger - Grodzisk Mazowiecki | 2022/08/14 13:20 | Olaf Pieczkowski v Christian Langmo | 6-7,6-2,4-6 |