Stadium: Court 3 Round: 2
| Coupe Davis | 2023/06/14 10:35 | Ivanovski, Kalin v Liam Delicata | 6-2,6-4 |
| ITF M25 Skopje | 2023/06/11 11:00 | Ivanovski, Kalin v Sascha Gueymard Wayenburg | 7-6,6-4 |
| ITF M25 Skopje | 2023/06/10 12:40 | Ergi Kirkin v Ivanovski, Kalin | 6-3,2-6,2-6 |
| 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 |
| Coupe Davis | 2023/06/14 09:25 | Menelaos Efstathiou v Cozbinov, Alexander | 6-7,7-5,2-6 |
| ITF - M15 Monastir | 2023/06/09 08:30 | Ryuki Matsuda v Cozbinov, Alexander | 2-6,7-5,6-3 |
| ITF - M15 Monastir | 2023/06/08 10:55 | Kalman Boyd v Cozbinov, Alexander | 3-6,4-6 |
| ITF - M15 Monastir | 2023/06/07 10:05 | Sean Hodkin v Cozbinov, Alexander | 1-6,7-5,5-7 |
| ITF - M15 Monastir | 2023/06/04 08:30 | Adrien Gobat v Cozbinov, Alexander | 1-6,4-6 |
| ITF - M15 Monastir | 2023/06/03 08:30 | Cozbinov, Alexander v Lambling, Raphael | 6-1,6-4 |
| ITF - M15 Monastir | 2023/06/02 08:30 | Alexis Gautier v Cozbinov, Alexander | 1-6,6-2,4-6 |
| ITF - M15 Monastir | 2023/06/01 11:00 | Florig, Philip v Cozbinov, Alexander | 0-6,3-6 |