Stadium: Centre Court Round: 19 Ground: Clay
| 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 Zug | 2023/07/23 15:25 | Vladyslav Orlov v Ugo Blanchet | 4-6,6-4,7-6 |
| Challenger Tampere | 2023/07/17 11:05 | Vladyslav Orlov v Ergi Kirkin | 6-7,3-6 |
| Challenger Tampere | 2023/07/16 10:30 | Vladyslav Orlov v Vesa Ahti | 6-4,6-4 |
| Challenger Salzburg | 2023/07/10 09:00 | Akira Santillan v Vladyslav Orlov | 6-3,6-1 |
| Challenger Salzburg | 2023/07/09 10:10 | Milos Karol v Vladyslav Orlov | 7-5,3-6,1-6 |
| Challenger Karlsruhe | 2023/07/02 13:25 | Tim Handel v Vladyslav Orlov | 6-4,6-4 |
| Challenger Luedenscheid | 2023/07/30 14:50 | Philip Florig v Tommaso Compagnucci | 5-7,4-6 |
| Challenger Zug | 2023/07/23 14:35 | Tommaso Compagnucci v Damien Wenger | 3-6,4-6 |
| ITF M25 Esch/Alzette | 2023/07/21 13:10 | Tommaso Compagnucci v Mikalai Haliak | 6-3,1-6,3-6 |
| ITF M25 Esch/Alzette | 2023/07/20 12:00 | Tommaso Compagnucci v Amaury Raynel | 6-3,6-0 |
| ITF M25 Esch/Alzette | 2023/07/19 10:55 | Tommaso Compagnucci v Gilles Kremer | 6-1,6-1 |
| ITF M25 Cattolica | 2023/06/21 13:55 | Kirill Kivattsev v Tommaso Compagnucci | 6-3,6-4 |
| ITF M25 Cattolica | 2023/06/20 08:00 | Federico Valle v Tommaso Compagnucci | 2-6,2-6 |
| ITF M15 Chieti | 2023/06/17 15:55 | Tommaso Compagnucci v Marcello Serafini | 3-6,2-6 |