Stadium: VR Bank Court 1 Round: 24 Ground: Hardcourt indoor
| Plovdiv, Singles Qualifying M-ITF-BUL-03A | 2019/06/07 07:30 | Dimitar Kuzmanov v Vladyslav Orlov | 7-5,2-6,6-3 |
| Challenger - Cherbourg | 2020/02/09 11:00 | Dimitar Kuzmanov v Arnaboldi, Andrea | 4-6,2-6 |
| ATP Cup, Playoffs | 2020/01/07 06:30 | Darcis, Steve v Dimitar Kuzmanov | 0-6,3-6 |
| ATP Cup, Playoffs | 2020/01/04 23:00 | Dimitar Kuzmanov v Cozbinov, Alexander | 6-1,7-5 |
| ATP Cup, Playoffs | 2020/01/03 07:55 | Cameron Norrie v Dimitar Kuzmanov | 6-2,3-6,6-2 |
| ITF - M15 Doha | 2019/12/15 16:00 | Dimitar Kuzmanov v Kalenichenko, Danylo | 6-0,6-4 |
| ITF - M15 Doha | 2019/12/13 12:00 | Aslan Karatsev v Dimitar Kuzmanov | 5-7,4-6 |
| ITF - M15 Doha | 2019/12/12 13:25 | Shyla, Yaraslau v Dimitar Kuzmanov | 0-6,1-6 |
| ITF - M15 Doha | 2019/12/11 10:00 | Oleksii Krutykh v Dimitar Kuzmanov | 1-6,7-6,4-6 |
| Challenger - Bengaluru | 2020/02/11 08:15 | Vladyslav Orlov v Blaz Rola | 5-7,3-6 |
| Challenger - Bengaluru | 2020/02/10 08:45 | Vladyslav Orlov v R Prabodh, Suraj | 6-2,6-2 |
| Nonthaburi, Singles M-ITF-THA-01A | 2020/02/05 08:25 | Vladyslav Orlov v Khumoyun Sultanov | 1-6,4-6 |
| Nonthaburi, Singles M-ITF-THA-01A | 2020/01/30 07:35 | Vladyslav Orlov v Khumoyun Sultanov | 6-7,6-7 |
| Nonthaburi, Singles M-ITF-THA-01A | 2020/01/28 05:25 | Congsup Congcar v Vladyslav Orlov | 4-6,3-6 |
| Bangkok, Thaïlande | 2020/01/15 04:30 | Vladyslav Orlov v Wu, Di | 6-2,4-6,3-6 |
| Bangkok, Thaïlande | 2020/01/14 05:35 | Brkic, Tomislav v Vladyslav Orlov | 7-6,4-6,1-6 |
| Bangkok, Thaïlande | 2020/01/12 03:00 | Vladyslav Orlov v Sookton-Eng, Chanchai | 6-0,6-2 |