Estadio: Center Court Round: 14 Ground: Clay
| Challenger de Troisdorf | 2023/05/29 10:40 | Benjamin Hassan v Liam Gavrielides | 6-1,6-3 |
| Challenger de Troisdorf | 2023/05/31 10:30 | Benjamin Hassan v Frederico Ferreira Silva | 3-6,6-3,2-6 |
| Challenger de Troisdorf | 2023/05/30 09:55 | Kaichi Uchida v Benjamin Hassan | 3-6,3-6 |
| Challenger de Troisdorf | 2023/05/29 10:40 | Benjamin Hassan v Liam Gavrielides | 6-1,6-3 |
| Challenger de Troisdorf | 2023/05/28 13:45 | Benjamin Hassan v Hazem Naw | 4-6,7-6,7-5 |
| Challenger de Skopie | 2023/05/23 11:00 | Sumit Nagal v Benjamin Hassan | 6-1,6-3 |
| Challenger de Oeiras | 2023/05/15 09:00 | Benjamin Hassan v Mate Valkusz | 7-5,3-6,1-6 |
| Challenger de Oeiras | 2023/05/14 09:00 | Benjamin Hassan v Henrique Rocha | 6-4,7-5 |
| Challenger de Mauthausen | 2023/05/08 08:00 | Benjamin Hassan v Hendrik Jebens | 2-6,6-7 |
| Challenger de Troisdorf | 2023/05/29 10:40 | Benjamin Hassan v Liam Gavrielides | 6-1,6-3 |
| Challenger de Troisdorf | 2023/05/28 12:15 | Liam Gavrielides v Manuel Guinard | 6-2,2-6,6-2 |
| ITF M15 Warmbad-Villach | 2023/05/25 08:25 | Khumoyun Sultanov v Liam Gavrielides | 6-7,6-2,6-4 |
| ITF M15 Warmbad-Villach | 2023/05/24 07:30 | Liam Gavrielides v Alexander Blockx | 6-4,6-2 |
| ITF M15 Warmbad-Villach | 2023/05/22 11:25 | Jonas Trinker v Liam Gavrielides | 1-6,2-6 |
| ITF M15 Warmbad-Villach | 2023/05/21 12:00 | Leonardo Mazzucchelli v Liam Gavrielides | 3-6,2-6 |
| ITF M15 Alaminos-Larnaca | 2023/05/11 08:00 | Sergis Kyratzis v Liam Gavrielides | 3-6,6-3,6-4 |
| ITF M15 Alaminos-Larnaca | 2023/05/10 09:35 | Philip Florig v Liam Gavrielides | 2-6,3-6 |