Stadium: Court 6 Round: 27 Ground: Clay
| ITF - Oldenzaal M25 | 2023/08/31 15:20 | Oliver Crawford v Stijn Slump | 6-4,6-2 |
| ITF - Oldenzaal M25 | 2023/08/30 17:35 | Oliver Crawford v Thiemo De Bakker | 3-6,6-1,6-3 |
| Challenger Augsburg | 2023/08/23 08:00 | Oliver Crawford v Carlos Taberner | 6-3,4-6,6-7 |
| Challenger Augsburg | 2023/08/22 08:00 | Oliver Crawford v Giovanni Fonio | 6-2,6-3 |
| ITF - Kramsach M25 | 2023/07/29 11:00 | Oliver Crawford v Gerard Campana Lee | 6-7,3-6 |
| ITF - Kramsach M25 | 2023/07/28 09:00 | Oliver Crawford v Peter Heller | 6-3,6-4 |
| ITF - Kramsach M25 | 2023/07/27 09:00 | Oliver Crawford v Hynek Barton | 7-6,3-6,6-4 |
| ITF - Kramsach M25 | 2023/07/26 10:30 | Oliver Crawford v Dario Huber | 6-3,6-4 |
| ITF - Oldenzaal M25 | 2023/08/31 11:00 | Aleksandr Braynin v Adam Panaras | 6-1,6-2 |
| ITF - Oldenzaal M25 | 2023/08/30 18:10 | Aleksandr Braynin v Guy Den Heijer | 4-6,7-6,7-5 |
| ITF - Poznań M25 | 2023/08/24 13:30 | Aleksandr Braynin v Lorenzo Joaquin Rodriguez | 4-6,4-6 |
| ITF - Poznań M25 | 2023/08/23 11:25 | Aleksandr Braynin v Pijus Vaitiekunas | 6-3,7-6 |
| Challenger Grodzisk Mazowiecki | 2023/08/13 08:00 | Denis Yevseyev v Aleksandr Braynin | 4-6,6-3,6-4 |
| Challenger Cordenons | 2023/08/07 11:15 | Aleksandr Braynin v Fausto Tabacco | 6-2,5-7,3-6 |
| Challenger Porto | 2023/07/31 10:00 | Aleksandr Braynin v Jaime Faria | 4-6,5-7 |
| Challenger Porto | 2023/07/30 12:20 | Daniel Cox v Aleksandr Braynin | 4-6,4-6 |