Stadium: Court 1 (Center) Round: 25 Ground: Clay
| 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 |
| ITF - M25 Kursumlijska Banja | 2023/05/10 09:00 | Ivanovski, Kalin v Viktor Jovic | 3-6,6-3,6-4 |
| Challenger - Prague | 2023/05/01 13:00 | Ivanovski, Kalin v Stricker, Dominic Stephan | 2-6,2-6 |
| ITF M25 Jablonec Nad Nisou | 2023/05/31 10:20 | Dominik Kellovsky v Tibo Colson | 7-5,3-6,7-6 |
| ITF - M25 Varnamo | 2023/05/11 08:15 | Tibo Colson v Lucas Catarina | 5-7,4-6 |
| ITF - M25 Varnamo | 2023/05/09 11:55 | Oskar Jansson v Tibo Colson | 0-6,4-6 |
| ITF - M15 Meerbusch | 2023/04/25 11:00 | Liam Gavrielides v Tibo Colson | 5-7,6-2,6-3 |
| ITF - M25 Trnava | 2023/04/01 09:00 | Tibo Colson v Karl Friberg | 2-6,4-6 |
| ITF - M25 Trnava | 2023/03/31 08:55 | Tibo Colson v Peter Benjamin Privara | 6-3,6-2 |
| ITF - M25 Trnava | 2023/03/30 10:00 | Recek, Dominik v Tibo Colson | 6-7,4-6 |
| ITF - M25 Trnava | 2023/03/28 13:05 | Tibo Colson v Samuel Kyjaci | 6-3,6-4 |