Stadium: 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 | Ivanovski, Kalin v Obrad Markovski | 6-3,4-6,4-6 |
| ITF M15 Skopje | 2021/05/31 12:30 | Battaglino, Stefano v Obrad Markovski | 6-2,5-7,10-7 |
| ITF M25 Kiseljak | 2021/05/23 07:00 | Micov, Stefan v Obrad Markovski | 6-3,6-7,10-5 |
| ITF - M15 Brcko | 2021/05/18 14:00 | Obrad Markovski v Tomas, Aleksandar | 4-6,1-6 |
| ITF - M15 Brcko | 2021/05/16 14:00 | Obrad Markovski v Ivic, Stefan | 6-4,6-2 |
| ITF - M15 Prijedor | 2021/05/09 12:30 | Kekez, Duje v Obrad Markovski | 6-4,6-3 |
| Sibenik, Singles M-ITF-CRO-05A | 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 | Prodanov, Denislav v Faivre, Pierre | 0-6,1-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/02 10:00 | Jules Marie v Prodanov, Denislav | 6-1,6-0 |
| ITF Bulgaria F1 Qual | 2017/05/07 09:00 | Prodanov, Denislav v Shandarov, Radoslav | 0-6,6-2,6-7 |