Ground: Hardcourt outdoor
| ATP Singapore | 2021/02/20 03:00 | Robert Galloway v Vladyslav Orlov | 6-4,6-4 |
| Challenger Barcelona | 2021/10/03 08:00 | Georgii Kravchenko v Vladyslav Orlov | 6-4,6-1 |
| Challenger Bukarest | 2021/09/19 11:35 | Dragos Nicolae Madaras v Vladyslav Orlov | 3-6,6-1,6-0 |
| Challenger Kyiv | 2021/09/06 09:45 | Vladyslav Orlov v Clement Tabur | 1-6,6-1,3-6 |
| Challenger Kyiv | 2021/09/05 09:30 | Vladyslav Orlov v Yan Bondarevskiy | 7-5,6-2 |
| Challenger Barletta | 2021/08/22 14:00 | Vladyslav Orlov v Luca Potenza | 4-6,6-4,5-7 |
| ITF M25 Bacau | 2021/08/21 09:35 | Vladyslav Orlov v Arthur Cazaux | 6-7,2-6 |
| ITF M25 Bacau | 2021/08/20 08:00 | Matias Zukas v Vladyslav Orlov | 2-6,3-6 |
| ITF M25 Bacau | 2021/08/19 11:00 | Stefan Palosi v Vladyslav Orlov | 6-7,3-6 |
| Challenger Porto | 2021/06/28 13:00 | Yosuke Watanuki v Robert Galloway | 6-1,6-1 |
| Challenger Porto | 2021/06/27 14:10 | Robert Galloway v Alexander Zhurbin | 6-2,6-2 |
| Challenger Orlando | 2021/06/06 16:50 | Robert Galloway v Stefan Kozlov | 4-6,6-7 |
| ATP Singapore | 2021/02/21 04:00 | Thai-Son Kwiatkowski v Robert Galloway | 6-2,6-3 |
| ATP Singapore | 2021/02/20 03:00 | Robert Galloway v Vladyslav Orlov | 6-4,6-4 |
| Challenger Poprad Tatry Qual | 2018/06/16 10:05 | Andreas Haider-Maurer v Robert Galloway | 6-4,7-5 |
| Challenger Loughborough Qual | 2018/05/19 13:30 | Robert Galloway v Jurij Rodionov | 0-6,5-7 |
| Challenger Lisbon Qual | 2018/05/13 14:35 | Joris De Loore v Robert Galloway | 6-1,6-1 |