Estadio: Court 6 Round: 25 Ground: Hardcourt outdoor
| Challenger de Bérgamo | 2023/10/29 15:40 | Ugo Blanchet v Andrea Picchione | 7-5,6-0 |
| Challenger de Ortisei | 2023/10/23 08:00 | Lukas Klein v Andrea Picchione | 7-6,4-6,6-2 |
| Challenger de Ortisei | 2023/10/22 10:40 | Aleksandr Braynin v Andrea Picchione | 3-6,4-6 |
| Challenger de Olbia | 2023/10/15 09:45 | Andrea Picchione v Adria Soriano Barrera | 1-6,6-3,6-4 |
| ITF M25 Santa Margarita | 2023/10/02 11:45 | Andrea Picchione v Buvaysar Gadamauri | 5-7,5-7 |
| ITF M25 Santa Margarita | 2023/09/27 10:40 | Andrea Picchione v Federico Bondioli | 3-6,2-6 |
| ITF M25 Santa Margarita | 2023/09/26 13:30 | Carlos Lopez Montagud v Andrea Picchione | 6-7,1-6 |
| Challenger de Bad Waltersdorf | 2023/09/19 13:05 | Vit Kopriva v Andrea Picchione | 6-4,3-6,7-6 |
| ITF M25 Monastir | 2023/11/07 08:30 | Jan Kupcic v Sven Corbinais | 6-2,6-1 |
| ITF M25 Monastir | 2023/11/06 09:05 | Jan Kupcic v Maj Premzl | 7-6,6-1 |
| ITF M25 Monastir | 2023/11/05 10:30 | Jan Kupcic v Pijus Vaitiekunas | 7-6,6-2 |
| ITF M15 Monastir | 2023/11/02 10:20 | Jan Kupcic v John Sperle | 2-6,6-7 |
| ITF M15 Monastir | 2023/11/01 08:00 | Sebastian Sorger v Jan Kupcic | 2-6,4-6 |
| ITF M15 Monastir | 2023/10/30 15:45 | Maurus Malgiaritta v Jan Kupcic | 2-6,1-6 |
| ITF M15 Monastir | 2023/10/30 08:00 | Stefan Peter Hampe v Jan Kupcic | 5-7,6-7 |
| ITF M15 Monastir | 2023/10/29 09:30 | Luka Bojicic Ono v Jan Kupcic | 1-6,2-6 |