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 Skopje | 2021/06/02 08:00 | Kalin Ivanovski v Alex Rybakov | 2-6,2-6 |
| ITF M15 Sibenik | 2021/05/19 12:30 | Rimpei Kawakami v Kalin Ivanovski | 6-0,6-2 |
| ITF M15 Sibenik | 2021/04/21 09:20 | Kalin Ivanovski v Lorenzo Bocchi | 7-6,4-6,6-7 |
| 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 Skopje | 2021/05/31 12:30 | Stefano Battaglino v Obrad Markovski | 6-2,5-7,10-7 |
| ITF M25 Kiseljak | 2021/05/23 07:00 | Stefan Micov v Obrad Markovski | 6-3,6-7,10-5 |
| ITF M15 Brcko | 2021/05/18 14:00 | Obrad Markovski v Aleksandar Tomas | 4-6,1-6 |
| ITF M15 Brcko | 2021/05/16 14:00 | Obrad Markovski v Stefan Ivic | 6-4,6-2 |
| ITF M15 Prijedor | 2021/05/09 12:30 | Duje Kekez v Obrad Markovski | 6-4,6-3 |
| ITF M15 Sibenik | 2021/04/18 13:00 | Borna Devald v Obrad Markovski | 6-3,5-7,10-7 |
| ITF M15 Sharm El Sheikh | 2021/04/04 09:30 | Obrad Markovski v Adam Jones | 0-6,4-6 |
| ITF M15 Sharm El Sheikh | 2021/03/29 07:30 | Obrad Markovski v Arvid Nordquist | 3-6,4-6 |