Stadium: Court 4 Round: 62 Ground: Clay
| ITF M15 Belgrade | 2022/06/26 08:15 | Tomislav Jotovski v Xian Yao Zhou | 6-1,6-2 |
| ITF M15 Skopje | 2022/06/14 11:50 | Tomislav Jotovski v Juan Pablo Paz | 2-6,3-6 |
| ITF M25 Skopje | 2022/06/09 08:00 | Jakub Paul v Tomislav Jotovski | 7-6,6-2 |
| ITF M25 Skopje | 2022/06/08 10:00 | Tomislav Jotovski v Oleksandr Bielinskyi | 6-3,6-2 |
| ITF M25 Skopje | 2022/06/07 07:55 | Tomislav Jotovski v Ioannis Kountourakis | 6-2,6-0 |
| ITF M25 Skopje | 2022/06/06 11:25 | Tomislav Jotovski v Ivan Kremenchutskyi | 4-6,6-4,10-4 |
| ITF M15 Doboj | 2022/05/09 08:00 | Tomislav Jotovski v Mihai Razvan Marinescu | 6-1,6-7,9-11 |
| ITF M25 Ulcinj | 2022/05/04 09:05 | Hamad Medjedovic v Tomislav Jotovski | 6-3,7-6 |
| ITF M15 Belgrade | 2022/06/26 08:15 | Ivailo Keremedchiev v Milan Drinic | 6-2,6-0 |
| 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 |