Stadium: Center Court Round: 25 Ground: Clay
| Challenger - Praag | 2023/05/01 13:00 | Kalin Ivanovski v Dominic Stephan Stricker | 2-6,2-6 |
| Challenger - Oeiras | 2023/04/16 12:30 | Billy Harris v Kalin Ivanovski | 6-2,4-6,6-4 |
| Challenger - Split | 2023/04/11 12:20 | Duje Ajdukovic v Kalin Ivanovski | 6-7,6-1,6-1 |
| ITF - M25 Dubrovnik | 2023/04/06 08:00 | Aldin Setkic v Kalin Ivanovski | 7-6,6-2 |
| ITF - M25 Dubrovnik | 2023/04/05 07:00 | Matteo Donati v Kalin Ivanovski | 6-1,3-6,0-6 |
| ITF M25 - Toulouse | 2023/03/23 10:00 | Kalin Ivanovski v Harry Wendelken | 1-6,6-7 |
| ITF M25 - Toulouse | 2023/03/21 13:00 | Kalin Ivanovski v Paul Inchauspe | 6-2,6-4 |
| ITF - M15 Poitiers | 2023/03/18 13:30 | Kalin Ivanovski v Sascha Gueymard Wayenburg | 2-6,6-7 |
| ITF - M15 Kursumlijska Banja | 2023/05/03 14:35 | Viktor Jovic v Nikita Mashtakov | 2-6,3-6 |
| ITF - M15 Kursumlijska Banja | 2023/05/02 09:00 | Viktor Jovic v Niklas Waldner | 6-1,6-3 |
| ITF - M15 Kursumlijska Banja | 2023/05/01 08:00 | Viktor Jovic v Alessandro Bellifemine | 6-4,6-3 |
| ITF - M15 Kursumlijska Banja | 2023/04/27 10:35 | Viktor Jovic v Duje Ajdukovic | 7-5,0-6,4-6 |
| ITF - M15 Kursumlijska Banja | 2023/04/26 16:00 | Viktor Jovic v Simone Agostini | 6-4,6-3 |
| UTR - Pro Beograd | 2023/04/22 11:27 | Viktor Jovic v Luka Pavlovic | 2-6,6-2,4-5 |
| UTR - Pro Beograd | 2023/04/21 06:00 | Viktor Jovic v Vanja Hodzic | 6-2,6-3 |
| UTR - Pro Beograd | 2023/04/19 06:00 | Viktor Jovic v Petr Nesterov | 6-4,3-6,5-6 |