Stadium: Court 2 Round: 26 Ground: Hardcourt outdoor
| ITF M25 Monastir | 2023/11/08 09:45 | Andrea Picchione v Jan Kupcic | 6-3,6-1 |
| Challenger Bergamo | 2023/10/29 15:40 | Ugo Blanchet v Andrea Picchione | 7-5,6-0 |
| Challenger Ortisei | 2023/10/23 08:00 | Lukas Klein v Andrea Picchione | 7-6,4-6,6-2 |
| Challenger Ortisei | 2023/10/22 10:40 | Aleksandr Braynin v Andrea Picchione | 3-6,4-6 |
| Challenger Olbia | 2023/10/15 09:45 | Andrea Picchione v Adria Soriano Barrera | 1-6,6-3,6-4 |
| ITF M25 Santa Margherita | 2023/10/02 11:45 | Andrea Picchione v Buvaysar Gadamauri | 5-7,5-7 |
| ITF M25 Santa Margherita | 2023/09/27 10:40 | Andrea Picchione v Federico Bondioli | 3-6,2-6 |
| ITF M25 Santa Margherita | 2023/09/26 13:30 | Carlos Lopez Montagud v Andrea Picchione | 6-7,1-6 |
| 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 M15 Sharm El Sheikh | 2023/10/25 07:00 | Philip Henning v Jiri Barnat | 6-2,6-1 |