| UTR Pro Tennis Series Sofia | 2021/09/02 11:30 | Ivailo Keremedchiev v Samuil Konov | 3-6,7-6,5-2 |
| UTR Pro Tennis Series Sofia | 2021/09/01 08:00 | Alec Adamson v Ivailo Keremedchiev | 4-6,1-5 |
| UTR Pro Tennis Series Sofia | 2021/08/31 08:00 | Dian Nedev v Ivailo Keremedchiev | 6-4,5-2 |
| UTR Pro Tennis Series Sofia | 2021/08/30 13:30 | Ivailo Keremedchiev v Alexandar Lazarov | 1-6,6-6 |
| ITF M15 Novi Sad | 2021/08/03 10:20 | Gorazd Srbljak v Ivailo Keremedchiev | 6-1,7-5 |
| ITF M15 Novi Sad | 2021/08/02 11:00 | Ivailo Keremedchiev v Taiyo Yamanaka | 6-2,6-7,10-6 |
| ITF M15 Novi Sad | 2021/08/01 09:45 | Lazar Vojinovic v Ivailo Keremedchiev | 4-6,6-3,6-10 |
| ITF M25 Fayetteville | 2020/11/02 17:30 | Justin Roberts v Ivailo Keremedchiev | 6-3,6-4 |
| UTR Pro Tennis Series Sofia | 2021/09/01 06:30 | Volodymyr Uzhylovskyi v George Lazarov | 1-6,6-1,1-5 |
| UTR Pro Tennis Series Sofia | 2021/08/31 09:30 | Volodymyr Uzhylovskyi v Warren Sinius | 6-2,5-4 |
| UTR Pro Tennis Series Sofia | 2021/08/30 13:30 | Valentin Vanta v Volodymyr Uzhylovskyi | 6-2,6-3 |
| UTR Pro Tennis Series Portoroz | 2021/08/27 12:00 | Vladan Tadic v Volodymyr Uzhylovskyi | 5-7,2-6 |
| UTR Pro Tennis Series Portoroz | 2021/08/26 07:00 | Nik Razborsek v Volodymyr Uzhylovskyi | 6-3,5-7,5-7 |
| UTR Pro Tennis Series Portoroz | 2021/08/25 10:00 | Olexiy Kolisnyk v Volodymyr Uzhylovskyi | 6-1,6-1 |
| UTR Pro Tennis Series Portoroz | 2021/08/17 12:30 | Volodymyr Uzhylovskyi v Max Lukman | 6-1,5-1 |
| ITF M15 Cairo | 2021/08/02 11:30 | Volodymyr Uzhylovskyi v Lautaro Agustin Falabella | 2-6,6-2,10-12 |