Stadium: Center Court Round: 14 Ground: Clay
| Challenger Troisdorf | 2023/05/30 16:15 | Henri Squire v Renzo Olivo | 2-6,5-7 |
| ITF M25 Most | 2023/05/28 08:00 | Timo Stodder v Henri Squire | 1-6,6-3,0-6 |
| ITF M25 Most | 2023/05/27 11:05 | Emilien Voisin v Henri Squire | 6-7,3-6 |
| ITF M25 Most | 2023/05/26 09:45 | Martin Damm v Henri Squire | 6-3,5-7,5-7 |
| ITF M25 Most | 2023/05/25 09:40 | Patrik Rikl v Henri Squire | 4-6,2-6 |
| ITF M25 Most | 2023/05/24 07:55 | Michael Agwi v Henri Squire | 0-6,0-6 |
| ITF M25 Prague | 2023/05/21 09:00 | Lukas Neumayer v Henri Squire | 6-2,6-3 |
| ITF M25 Prague | 2023/05/19 10:30 | Michael Vrbensky v Henri Squire | 1-6,0-6 |
| ITF M25 Most | 2023/05/24 10:45 | Martin Damm v Aleksandr Braynin | 6-3,6-4 |
| ITF M25 Most | 2023/05/23 08:00 | Aleksandr Braynin v Matyas Cerny | 6-1,3-6,5-10 |
| ITF M25 Most | 2023/05/22 08:00 | Aleksandr Braynin v Roman Ruenger | 7-5,6-3 |
| Challenger Turin | 2023/05/16 16:00 | Aleksandr Braynin v Flavio Cobolli | 3-6,3-6 |
| Challenger Turin | 2023/05/14 10:00 | Aleksandr Braynin v Kristjan Tamm | 1-6,6-3,6-4 |
| ITF M25 Valldoreix | 2023/05/10 10:15 | Aleksandr Braynin v Maxwell Exsted | 6-3,1-6,2-6 |
| ITF M25 Valldoreix | 2023/05/09 08:00 | Aleksandr Braynin v Nikolay Nedelchev | 7-6,6-2 |
| ITF M25 Valldoreix | 2023/05/08 09:00 | Aleksandr Braynin v Peetu Pohjola | 6-0,6-2 |