Stadium: Court 1 (Center) Round: 26 Ground: Clay
| ITF M25 Skopje | 2023/06/07 12:15 | Kalin Ivanovski v Tibo Colson | 4-6,6-2,6-4 |
| Challenger Skopje | 2023/05/23 10:00 | Kalin Ivanovski v Dino Prizmic | 4-6,1-6 |
| ITF M25 Kursumlijska Banja | 2023/05/18 13:00 | Mikalai Haliak v Kalin Ivanovski | 6-4,1-6,6-3 |
| ITF M25 Kursumlijska Banja | 2023/05/14 10:45 | Clement Tabur v Kalin Ivanovski | 6-4,3-6,6-2 |
| ITF M25 Kursumlijska Banja | 2023/05/13 08:00 | Oleksandr Ovcharenko v Kalin Ivanovski | 5-7,2-6 |
| ITF M25 Kursumlijska Banja | 2023/05/12 08:00 | Kalin Ivanovski v Hady Habib | 7-6,7-5 |
| ITF M25 Kursumlijska Banja | 2023/05/11 08:30 | Timo Legout v Kalin Ivanovski | 6-2,1-6,0-6 |
| ITF M25 Kursumlijska Banja | 2023/05/10 09:00 | Kalin Ivanovski v Viktor Jovic | 3-6,6-3,6-4 |
| ITF M25 Skopje | 2023/06/07 12:25 | Hans Albert Schubert v Alen Bill | 3-6,1-6 |
| ITF M25 Skopje | 2023/06/06 07:30 | Alen Bill v Veljko Krstic | 6-4,6-2 |
| ITF M25 Skopje | 2023/06/05 08:00 | Alen Bill v Johannes Prammer | 6-1,6-1 |
| ITF M25 Skopje | 2023/06/04 09:30 | Alen Bill v Boris Stojanovic | 6-1,6-1 |
| ITF M15 Prijedor | 2023/05/15 11:30 | Alen Bill v Ali Habib | 7-6,2-6,7-10 |
| ITF M15 Doboj | 2023/05/08 10:30 | Alen Bill v Nikola Basic | 2-6,4-6 |
| ITF M15 Doboj | 2023/05/07 10:30 | Dzenan Bakovic v Alen Bill | 2-6,3-6 |
| ITF M15 Osijek | 2023/05/01 10:10 | Radomir Tomic v Alen Bill | 6-0,6-3 |