Stadium: Court 3 Round: 2 Ground: Hardcourt indoor
| Davis Cup | 2023/06/14 10:35 | Kalin Ivanovski v Liam Delicata | 6-2,6-4 |
| ITF M25 Skopje | 2023/06/11 11:00 | Kalin Ivanovski v Sascha Gueymard Wayenburg | 7-6,6-4 |
| ITF M25 Skopje | 2023/06/10 12:40 | Ergi Kirkin v Kalin Ivanovski | 6-3,2-6,2-6 |
| ITF M25 Skopje | 2023/06/08 11:50 | Kalin Ivanovski v Alen Bill | 6-0,6-0 |
| 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 |
| Davis Cup | 2023/06/14 09:25 | Menelaos Efstathiou v Alexander Cozbinov | 6-7,7-5,2-6 |
| ITF M15 Monastir | 2023/06/09 08:30 | Ryuki Matsuda v Alexander Cozbinov | 2-6,7-5,6-3 |
| ITF M15 Monastir | 2023/06/08 10:55 | Kalman Boyd v Alexander Cozbinov | 3-6,4-6 |
| ITF M15 Monastir | 2023/06/07 10:05 | Sean Hodkin v Alexander Cozbinov | 1-6,7-5,5-7 |
| ITF M15 Monastir | 2023/06/04 08:30 | Adrien Gobat v Alexander Cozbinov | 1-6,4-6 |
| ITF M15 Monastir | 2023/06/03 08:30 | Alexander Cozbinov v Raphael Lambling | 6-1,6-4 |
| ITF M15 Monastir | 2023/06/02 08:30 | Alexis Gautier v Alexander Cozbinov | 1-6,6-2,4-6 |
| ITF M15 Monastir | 2023/06/01 11:00 | Philip Florig v Alexander Cozbinov | 0-6,3-6 |