Stadium: Court 4 Round: 25 Ground: Hardcourt outdoor
| Challenger - Liberec | 2023/07/31 08:00 | Kirill Kivattsev v Matthew Dellavedova | 6-4,6-2 |
| Challenger - Liberec | 2023/07/30 08:00 | Pawel Juszczak v Matthew Dellavedova | 5-7,2-6 |
| ITF M15 Metzingen | 2023/07/25 10:55 | Liam Gavrielides v Matthew Dellavedova | 6-2,7-5 |
| Challenger - Tampere | 2023/07/17 09:00 | Matthew Dellavedova v Lorenzo Rottoli | 6-7,6-3,2-6 |
| Challenger - Tampere | 2023/07/16 09:25 | Dmitry Popko v Matthew Dellavedova | 7-6,2-6,5-7 |
| Challenger Braunchsweig | 2023/07/09 12:30 | Matthew Dellavedova v August Holmgren | 4-6,6-7 |
| Challenger - Karlsruhe | 2023/07/03 09:00 | Matthew Dellavedova v Hady Habib | 3-6,7-5,2-6 |
| Challenger - Karlsruhe | 2023/07/02 11:25 | Kenny de Schepper v Matthew Dellavedova | 6-7,6-1,5-7 |
| ITF M25 Roehampton | 2023/08/07 12:00 | Adam Jones v Ali Habib | 5-7,7-6,5-10 |
| ITF M25 Roehampton | 2023/08/06 13:00 | Freddie Ridout v Ali Habib | 3-6,2-6 |
| ITF M25 Roehampton | 2023/08/01 16:15 | Ali Habib v Devin Badenhorst | 4-6,6-7 |
| ITF M25 Roehampton | 2023/07/31 09:00 | Oliver Hague v Ali Habib | 6-7,4-6 |
| ITF M25 Roehampton | 2023/07/30 09:00 | Freddie Ridout v Ali Habib | 1-6,2-6 |
| ITF M25 Roehampton | 2023/07/16 14:20 | Liam Hignett v Ali Habib | 3-6,6-3,10-2 |
| ITF M25 Nottingham | 2023/07/11 14:00 | Luke Simkiss v Ali Habib | 6-1,6-2 |
| ITF M25 Nottingham | 2023/07/10 12:00 | James Davis v Ali Habib | 4-6,2-6 |