Stadium: Court 1 (Center) Round: 28 Ground: Clay
| ITF M25 Skopje | 2023/06/09 09:30 | Zekic, Miljan v Ergi Kirkin | 2-6,4-6 |
| ITF M25 Skopje | 2023/06/08 10:25 | Gorazd Srbljak v Ergi Kirkin | 1-6,3-6 |
| ITF M15 Prijedor | 2023/05/20 07:00 | Ergi Kirkin v Stefan Popovic | 4-6,2-6 |
| ITF M15 Prijedor | 2023/05/19 08:25 | Ergi Kirkin v Igor Gimenez | 3-6,7-5,11-9 |
| ITF M15 Prijedor | 2023/05/18 12:10 | Ergi Kirkin v Hayato Matsuoka | 6-1,6-0 |
| ITF - M15 Doboj | 2023/05/14 12:00 | Ergi Kirkin v Sebastian Sorger | 7-6,7-5 |
| ITF - M15 Doboj | 2023/05/13 07:30 | Ergi Kirkin v Stefan Popovic | 2-6,6-3,6-4 |
| ITF - M15 Doboj | 2023/05/12 07:00 | Ergi Kirkin v Hayato Matsuoka | 6-1,6-1 |
| ITF M25 Skopje | 2023/06/08 11:50 | Ivanovski, Kalin v Alen Bill | 6-0,6-0 |
| ITF M25 Skopje | 2023/06/07 12:15 | Ivanovski, Kalin v Tibo Colson | 4-6,6-2,6-4 |
| Challenger Skopje | 2023/05/23 10:00 | Ivanovski, Kalin v Dino Prizmic | 4-6,1-6 |
| ITF - M25 Kursumlijska Banja | 2023/05/18 13:00 | Mikalai Haliak v Ivanovski, Kalin | 6-4,1-6,6-3 |
| ITF - M25 Kursumlijska Banja | 2023/05/14 10:45 | Clement Tabur v Ivanovski, Kalin | 6-4,3-6,6-2 |
| ITF - M25 Kursumlijska Banja | 2023/05/13 08:00 | Oleksandr Ovcharenko v Ivanovski, Kalin | 5-7,2-6 |
| ITF - M25 Kursumlijska Banja | 2023/05/12 08:00 | Ivanovski, Kalin v Hady Habib | 7-6,7-5 |
| ITF - M25 Kursumlijska Banja | 2023/05/11 08:30 | Timo Legout v Ivanovski, Kalin | 6-2,1-6,0-6 |