Stadium: Court 8 Round: 62 Ground: Clay
| ITF M25 Skopje | 2022/06/06 10:15 | Bogdan Pavel v Ivailo Keremedchiev | 6-3,6-4 |
| ITF M25 Skopje | 2022/06/05 08:00 | Ivailo Keremedchiev v Aleksandar Mihailovic | 6-4,6-2 |
| UTR Pro Tennis Series Sofia | 2021/09/03 10:00 | Ivailo Keremedchiev v Volodymyr Uzhylovskyi | 3-6,6-6 |
| 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 M25 Skopje | 2022/06/07 09:25 | Oleksandr Bielinskyi v Trey Hilderbrand | 6-2,1-6,14-12 |
| ITF M25 Skopje | 2022/06/06 08:00 | Dino Vucidolov v Trey Hilderbrand | 2-6,1-6 |
| ITF M25 Kiseljak | 2022/05/31 10:00 | Pietro Pampanin v Trey Hilderbrand | 6-7,6-3,5-10 |
| ITF M25 Kiseljak | 2022/05/30 09:30 | Sasa Markovic v Trey Hilderbrand | 6-2,3-6,2-10 |
| ITF M25 Kiseljak | 2022/05/29 08:00 | Grygorii Kysilov v Trey Hilderbrand | 1-6,3-6 |
| ITF M15 Bucharest | 2022/05/25 06:50 | Trey Hilderbrand v Marvin Netuschil | 6-4,4-6,6-7 |
| ITF M15 Bucharest | 2022/05/23 08:00 | Trey Hilderbrand v Vlad Stoica | 7-6,6-3 |
| ITF M15 Bucharest | 2022/05/22 13:00 | Trey Hilderbrand v Dario Alexandru Ciobotaru | 6-3,6-4 |