Stadion: Court 1 Round: 44 Ground: Clay
| ITF - M15 - Skopje | 2021/06/11 07:00 | Alexis Gautier v Obrad Markovski | 6-4,6-3 |
| ITF - M15 - Skopje | 2021/06/10 08:35 | Kalin Ivanovski v Obrad Markovski | 6-3,4-6,4-6 |
| 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 |
| UTR Pro Tennis Series - Pazardzhik | 2021/04/03 08:30 | Denislav Prodanov v Pierre Faivre | 0-6,1-6 |
| UTR Pro Tennis Series - Pazardzhik | 2021/04/02 10:00 | Jules Marie v Denislav Prodanov | 6-1,6-0 |
| ITF - Bulgarien F1 - Qualifikation | 2017/05/07 09:00 | Denislav Prodanov v Radoslav Shandarov | 0-6,6-2,6-7 |