Stadium: Saturn Center Court Round: 25 Ground: Clay
| Challenger Meerbusch | 2022/08/09 13:50 | Henri Squire v Adrian Andreev | 2-6,4-6 |
| 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 Prague | 2023/05/18 08:55 | Petr Nouza v Henri Squire | 4-6,7-5,4-6 |
| French Open | 2023/05/26 10:25 | Genaro Alberto Olivieri v Adrian Andreev | 6-1,5-7,6-4 |
| French Open | 2023/05/24 14:20 | Adrian Andreev v Juan Pablo Ficovich | 6-2,7-5 |
| French Open | 2023/05/23 11:05 | Francesco Maestrelli v Adrian Andreev | 3-6,4-6 |
| Challenger Oeiras | 2023/05/15 15:05 | Radu Albot v Adrian Andreev | 6-1,6-3 |
| Challenger Mauthausen | 2023/05/08 15:00 | Adrian Andreev v Leandro Riedi | 7-6,4-6,6-7 |
| Challenger Oeiras | 2023/04/19 09:00 | Kaichi Uchida v Adrian Andreev | 6-1,1-6,6-2 |
| Challenger Oeiras | 2023/04/17 14:45 | Harold Mayot v Adrian Andreev | 3-6,4-6 |
| Challenger Las Franquesas del Valles | 2023/03/22 10:20 | Adrian Andreev v Gastao Elias | 4-6,3-6 |