Stadium: Court 3 Round: 27 Ground: Hardcourt outdoor
| 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 M15 Sharm El Sheikh | 2023/10/26 07:00 | Daniel Khazime v Philip Henning | 6-3,7-6 |
| ITF M25 Monastir | 2023/11/09 08:30 | Aziz Ouakaa v Ryan Nijboer | 2-6,3-6 |
| ITF M25 Monastir | 2023/11/08 08:30 | Aleksandr Lobanov v Ryan Nijboer | 2-6,6-4,1-6 |
| Challenger Bergamo | 2023/10/29 14:30 | Mark Lajal v Ryan Nijboer | 3-6,6-4,7-6 |
| Challenger Ortisei | 2023/10/24 13:40 | Ryan Nijboer v Daniil Glinka | 3-6,6-7 |
| Challenger Ortisei | 2023/10/23 12:30 | Stefano D'Agostino v Ryan Nijboer | 4-6,7-6,2-6 |
| Challenger Ortisei | 2023/10/22 14:40 | Patric Prinoth v Ryan Nijboer | 4-6,2-6 |
| Challenger Olbia | 2023/10/16 10:50 | Mathias Bourgue v Ryan Nijboer | 6-2,7-5 |
| Challenger Olbia | 2023/10/15 12:30 | Oscar Weightman v Ryan Nijboer | 6-2,6-7,4-6 |