Stadium: Court 5 Round: 25 Ground: Clay
| ITF M15 Porec | 2020/03/08 09:10 | Obrad Markovski v Kalin Ivanovski | 3-6,1-6 |
| ITF M15 Monastir | 2021/01/12 09:00 | Yusuke Takahashi v Kalin Ivanovski | 6-2,6-4 |
| ITF M15 Heraklion | 2020/11/21 13:00 | Kalin Ivanovski v Adrian Andreev | 1-6,4-6 |
| ITF M15 Heraklion | 2020/11/19 09:35 | Lucas Gerch v Kalin Ivanovski | 6-7,6-7 |
| ITF M15 Heraklion | 2020/11/18 12:30 | Kalin Ivanovski v Stefan Palosi | 7-5,6-2 |
| ITF M15 Heraklion | 2020/11/12 11:00 | Stuart Parker v Kalin Ivanovski | 6-2,6-0 |
| ITF M15 Heraklion | 2020/11/01 10:00 | Kalin Ivanovski v Nicholas David Ionel | 4-6,2-6 |
| Adriatic Tennis Series | 2020/06/16 14:30 | Carlos Gomez-Herrera v Kalin Ivanovski | 6-2,6-0 |
| ITF M15 Porec | 2020/03/09 09:00 | Pawel Juszczak v Kalin Ivanovski | 1-6,6-3,10-3 |
| ITF M15 Porec | 2020/03/08 09:10 | Obrad Markovski v Kalin Ivanovski | 3-6,1-6 |
| ITF M15 Antalya | 2020/02/16 07:00 | Obrad Markovski v Mats Hermans | 2-6,6-2,7-10 |
| ITF M15 Antalya | 2020/02/13 07:30 | Obrad Markovski v Edoardo Eremin | 3-6,2-6 |
| ITF M15 Antalya | 2020/02/02 09:00 | Obrad Markovski v Esteban Bruna | 6-7,6-4,8-10 |
| ITF M15 Zlatibor | 2019/09/16 10:30 | Obrad Markovski v Dusan Obradovic | 4-6,3-6 |
| ITF M15 Zlatibor | 2019/09/15 10:30 | Obrad Markovski v Xin Hu | 6-2,6-0 |
| ITF M15 Brasov | 2019/09/08 09:30 | Robert Damian Savin v Obrad Markovski | 6-3,7-6 |
| ITF M15 Curtea de Arges | 2019/08/19 06:30 | Dmitrii Baskov v Obrad Markovski | 4-6,6-3,10-8 |