Stadium: Center Court Round: 28 Ground: Hardcourt outdoor
| ITF M25 Monastir | 2023/11/10 08:30 | Philip Henning v Ryan Nijboer | 6-2,6-4 |
| ITF M25 Monastir | 2023/11/09 08:30 | Andrea Picchione v Philip Henning | 3-6,6-4,3-6 |
| ITF M25 Monastir | 2023/11/08 08:30 | Philip Henning v Romeo Hadzimehmedovic | 6-3,6-0 |
| ITF M25 Monastir | 2023/11/07 10:25 | Philip Henning v Teymuraz Gabashvili | 6-0,6-2 |
| ITF M25 Monastir | 2023/11/06 08:00 | Philip Henning v Saba George Nanobashvili | 6-1,6-1 |
| ITF M25 Monastir | 2023/11/05 10:30 | Philip Henning v Aleksei Mokrov | 6-2,6-1 |
| ITF M25 Sharm El Sheikh | 2023/11/01 10:15 | Philip Henning v Robert Strombachs | 6-7,6-3,2-6 |
| ITF M25 Sharm El Sheikh | 2023/10/31 10:40 | Philip Henning v Pietro Mugelli | 6-2,6-2 |
| ITF M25 Monastir | 2023/11/10 08:30 | Stijn Slump v Hady Habib | 4-6,2-6 |
| ITF M25 Monastir | 2023/11/09 08:30 | Tiago Pereira v Hady Habib | 4-6,2-6 |
| ITF M25 Monastir | 2023/11/08 12:10 | Alexey Nesterov v Hady Habib | 6-3,1-6,2-6 |
| Challenger Bergamo | 2023/10/29 17:15 | Nikoloz Basilashvili v Hady Habib | 6-4,6-1 |
| Challenger Ortisei | 2023/10/22 11:10 | Hady Habib v Luca Giacomini | 5-7,3-6 |
| Challenger Hamburg | 2023/10/16 12:45 | Lucas Gerch v Hady Habib | 6-2,6-4 |
| Challenger Hamburg | 2023/10/15 17:55 | Jakub Paul v Hady Habib | 6-3,2-6,2-6 |
| ITF M25 Rodez | 2023/10/13 15:00 | Hady Habib v Daniil Glinka | 6-7,4-6 |