| Challenger Iasi | 07/14 13:55 | 27 | [370] Kalin Ivanovski v Steven Diez [278] | 4-6,3-6 | |
| Challenger Iasi | 07/12 16:00 | 26 | [312] Filip C Jianu v Kalin Ivanovski [370] | 6-3,4-6,3-6 | |
| Challenger Iasi | 07/11 15:30 | 25 | [370] Kalin Ivanovski v Nicholas D Ionel [192] | 4-6,7-6,6-2 | |
| Challenger Iasi | 07/10 08:20 | 19 | [370] Kalin Ivanovski v Dan Alexandru Tomescu [439] | 7-6,7-6 | |
| Challenger Iasi | 07/09 10:20 | 14 | [370] Kalin Ivanovski v Brandon Walkin [211] | 6-2,6-2 | |
| Challenger - Troyes | 07/02 12:10 | 14 | Kalin Ivanovski v Giuseppe Tresca | 4-6,6-7 | |
| Challenger - Poznan | 06/18 08:30 | 14 | [184] Kai Wehnelt v Kalin Ivanovski [412] | 6-3,3-6,6-3 | |
| Taça Davis | 06/15 10:00 | 2 | [412] Kalin Ivanovski v Alexander Cozbinov [459] | 5-7,2-5 | |
| Taça Davis | 06/14 10:35 | 2 | Kalin Ivanovski v Liam Delicata | 6-2,6-4 | |
| ITF - M25 Skopje | 06/11 11:00 | 29 | [421] Kalin Ivanovski v Sascha Gueymard Wayenburg [398] | 7-6,6-4 | |
| ITF - M25 Skopje | 06/10 12:40 | 28 | [473] Ergi Kirkin v Kalin Ivanovski [421] | 6-3,2-6,2-6 | |
| ITF - M25 Skopje | 06/09 11:30 | 27 | Kalin Ivanovski v Mirza Basic | Walkover | |
| ITF - M25 Skopje | 06/08 11:50 | 26 | Kalin Ivanovski v Alen Bill | 6-0,6-0 | |
| ITF - M25 Skopje | 06/07 12:15 | 25 | Kalin Ivanovski v Tibo Colson | 4-6,6-2,6-4 | |
| Challenger - Escópia | 05/23 10:00 | 25 | [415] Kalin Ivanovski v Dino Prizmic [295] | 4-6,1-6 | |
| ITF - M25 Kuršumlijska Banja | 05/18 13:00 | 26 | Mikalai Haliak v Kalin Ivanovski | 6-4,1-6,6-3 | |
| ITF - M25 Kuršumlijska Banja | 05/17 09:05 | 25 | Matija Zugic v Kalin Ivanovski | Retired | |
| ITF - M25 Kuršumlijska Banja | 05/14 10:45 | 29 | [410] Clement Tabur v Kalin Ivanovski [459] | 6-4,3-6,6-2 | |
| ITF - M25 Kuršumlijska Banja | 05/13 08:00 | 28 | [416] Oleksandr Ovcharenko v Kalin Ivanovski [459] | 5-7,2-6 | |
| ITF - M25 Kuršumlijska Banja | 05/12 08:00 | 27 | Kalin Ivanovski v Hady Habib | 7-6,7-5 | |
| ITF - M25 Kuršumlijska Banja | 05/11 08:30 | 26 | [414] Timo Legout v Kalin Ivanovski [459] | 6-2,1-6,0-6 | |
| ITF - M25 Kuršumlijska Banja | 05/10 09:00 | 25 | Kalin Ivanovski v Viktor Jovic | 3-6,6-3,6-4 | |
| Challenger - Praga | 05/01 13:00 | 25 | [461] Kalin Ivanovski v Dominic Stricker [129] | 2-6,2-6 | |
| Challenger - Ostrava | 04/23 12:30 | 14 | Guido Andreozzi v Kalin Ivanovski | Cancelled | |
| Challenger - Oeiras | 04/16 12:30 | 14 | [310] Billy Harris v Kalin Ivanovski [463] | 6-2,4-6,6-4 | |
| Challenger - Split | 04/11 12:20 | 25 | Duje Ajdukovic v Kalin Ivanovski | 6-7,6-1,6-1 | |
| ITF - M25 Dubrovnik | 04/06 08:00 | 26 | Aldin Setkic v Kalin Ivanovski | 7-6,6-2 | |
| ITF - M25 Dubrovnik | 04/05 07:00 | 25 | Matteo Donati v Kalin Ivanovski | 6-1,3-6,0-6 | |
| ITF - M25 Toulouse | 03/23 10:00 | 26 | Kalin Ivanovski v Harry Wendelken | 1-6,6-7 | |
| ITF - M25 Toulouse | 03/21 13:00 | 25 | Kalin Ivanovski v Paul Inchauspe | 6-2,6-4 |