Stadium: Court 3 Round: 62 Ground: Clay
| ITF M15 Skopje | 2022/06/14 08:00 | Franco Roncadelli v Ivailo Keremedchiev | 6-4,6-3 |
| ITF M15 Skopje | 2022/06/12 08:00 | Ivailo Keremedchiev v Trey Hilderbrand | 7-6,6-1 |
| 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 |
| ITF M15 Monastir | 2021/12/21 08:00 | Milan Drinic v Boris Butulija | 4-6,6-7 |
| ITF M15 Novi Sad | 2021/08/04 08:00 | Mate Valkusz v Milan Drinic | 6-4,6-3 |
| ITF M15 Novi Sad | 2021/08/03 08:00 | Eric Morris v Milan Drinic | 1-6,2-6 |
| ITF M15 Novi Sad | 2021/08/02 08:00 | Berk Ilkel v Milan Drinic | 2-6,1-6 |
| ITF M15 Novi Sad | 2021/07/25 07:00 | Milan Drinic v Franco Roncadelli | 5-7,3-6 |
| ITF M15 Monastir | 2021/04/11 12:00 | Youcef Rihane v Milan Drinic | 7-6,6-2 |
| ITF M15 Monastir | 2021/02/28 10:30 | Luigi Castelletti v Milan Drinic | 4-6,0-6 |
| ITF M15 Monastir | 2021/02/21 12:00 | Milan Drinic v Niklas Guttau | 4-6,4-6 |