Stadium: Center Court Round: 19 Ground: Hardcourt outdoor
| Challenger Istanbul | 2023/09/03 11:50 | Vladyslav Orlov v Berk Ilkel | 6-2,6-2 |
| ITF M25 Poznan | 2023/08/23 12:05 | Michal Mikula v Vladyslav Orlov | 2-6,3-6 |
| ITF M25 Bielsko Biala | 2023/08/17 10:30 | Viacheslav Bielinskyi v Vladyslav Orlov | 6-3,6-2 |
| ITF M25 Bielsko Biala | 2023/08/16 10:40 | Fryderyk Lechno-Wasiutynski v Vladyslav Orlov | 6-7,2-6 |
| Challenger Cordenons | 2023/08/08 17:30 | Vladyslav Orlov v Matteo Gigante | 7-6,4-6,4-6 |
| Challenger Luedenscheid | 2023/07/31 16:10 | Vladyslav Orlov v Tommaso Compagnucci | 5-7,7-6,4-6 |
| Challenger Luedenscheid | 2023/07/30 13:10 | Vladyslav Orlov v Moritz Pieper | 6-4,6-2 |
| Challenger Zug | 2023/07/24 12:10 | Gianmarco Ferrari v Vladyslav Orlov | 6-3,6-4 |
| Challenger Istanbul | 2023/09/03 09:45 | Boris Butulija v Blaise Bicknell | 2-6,2-6 |
| Challenger Lima | 2023/08/26 22:00 | Blaise Bicknell v Alvaro Guillen Meza | 6-7,1-6 |
| Challenger Lima | 2023/08/25 21:25 | Blaise Bicknell v Murkel Dellien | 3-6,7-6,6-3 |
| Challenger Lima | 2023/08/24 23:35 | Blaise Bicknell v Ignacio Buse | 3-6,7-6,6-4 |
| Challenger Lima | 2023/08/23 17:30 | Juan Pablo Ficovich v Blaise Bicknell | 5-7,6-4,3-6 |
| Challenger Lima | 2023/08/22 15:00 | Blaise Bicknell v Victor Lilov | 6-2,6-4 |
| Challenger Winnipeg | 2023/08/14 17:30 | Omni Kumar v Blaise Bicknell | 6-1,6-2 |
| Challenger Winnipeg | 2023/08/13 20:40 | Osgar O'Hoisin v Blaise Bicknell | 2-6,4-6 |