Stadium: Court 2 Round: 26 Ground: Hardcourt outdoor
| ITF - M15 Sharm El Sheikh | 2020/10/21 09:30 | Felix Corwin v Marko Miladinovic | 3-6,6-2,4-6 |
| Campionatul Europei de Est | 2020/07/31 09:35 | Dimitar Kuzmanov v Marko Miladinovic | 6-2,6-0 |
| Campionatul Europei de Est | 2020/07/29 12:30 | Marko Miladinovic v Boris Butulija | 6-1,6-3 |
| Campionatul Europei de Est | 2020/07/27 11:00 | Marko Miladinovic v Vladan Tadic | 7-5,6-1 |
| Campionatul Europei de Est | 2020/06/24 08:00 | Marko Miladinovic v Matej Sabanov | 2-6,5-7 |
| Campionatul Europei de Est | 2020/06/23 08:00 | Mirza Basic v Marko Miladinovic | 6-2,6-3 |
| Campionatul Europei de Est | 2020/06/22 08:00 | Ricardas Berankis v Marko Miladinovic | 6-0,6-1 |
| Campionatul Europei de Est | 2020/06/17 18:00 | Marko Miladinovic v Alexandar Lazarov | 0-6,2-6 |
| ITF - M15 Sharm El Sheikh | 2020/10/21 10:30 | Aidan Mchugh v Vladyslav Orlov | 3-6,5-7 |
| Challenger Split | 2020/09/26 12:00 | Pedja Krstin v Vladyslav Orlov | 6-3,6-1 |
| Challenger - Sibiu | 2020/09/20 09:00 | Vladyslav Orlov v Ergi Kirkin | 6-2,4-6,1-6 |
| Challenger - Sibiu | 2020/09/19 11:10 | Vladyslav Orlov v Pol Toledo Bague | 4-6,6-0,6-2 |
| ITF - M15 Novomoskovsk | 2020/09/03 07:00 | Wojciech Marek v Vladyslav Orlov | 1-6,6-2,6-3 |
| ITF - M15 Novomoskovsk | 2020/09/02 07:00 | Michael Zhu v Vladyslav Orlov | 2-6,1-6 |
| German Premier League | 2020/08/21 10:15 | Vladyslav Orlov v Elmar Ejupovic | 4-6,4-6 |
| German Premier League | 2020/08/20 12:35 | Vladyslav Orlov v Mats Rosenkranz | 4-6,4-6 |