Stadium: Indoor 3 Round: 26 Ground: Clay
| ITF M25 Reggio Emilia | 2023/05/17 10:00 | Gian Marco Ortenzi v Kai Wehnelt | 0-6,2-6 |
| ITF M25 Reggio Emilia | 2023/05/15 16:30 | Kai Wehnelt v Federico Marchetti | 6-1,6-0 |
| ITF M25 Reggio Emilia | 2023/05/15 09:50 | Kai Wehnelt v Noah Perfetti | 6-3,3-6,10-6 |
| Challenger Francavilla | 2023/05/07 16:40 | Stefano Travaglia v Kai Wehnelt | 6-4,6-2 |
| ITF M25 Santa Margherita | 2023/05/01 11:00 | Sebastian Fanselow v Kai Wehnelt | 4-6,7-6,6-3 |
| ITF M25 Santa Margherita | 2023/04/24 10:40 | Kai Wehnelt v Andrey Chepelev | 3-6,4-6 |
| ITF M25 Santa Margherita | 2023/04/20 07:55 | Kai Wehnelt v Alexander Weis | 4-6,6-1,6-7 |
| ITF M25 Santa Margherita | 2023/04/19 11:55 | Federico Iannaccone v Kai Wehnelt | 6-7,4-6 |
| ITF M25 Reggio Emilia | 2023/05/17 07:30 | Giorgio Ricca v Federico Arnaboldi | 3-6,4-6 |
| Challenger Rome | 2023/04/24 12:25 | Federico Arnaboldi v Marco Trungelliti | 4-6,3-6 |
| Challenger Roseto | 2023/04/18 13:30 | Edoardo Lavagno v Federico Arnaboldi | 6-2,4-6,6-1 |
| Challenger Roseto | 2023/04/16 09:55 | Andrea Picchione v Federico Arnaboldi | 4-6,6-7 |
| Challenger Barletta | 2023/04/03 12:10 | Federico Arnaboldi v Shintaro Mochizuki | 2-6,3-6 |
| Challenger Sanremo | 2023/03/28 13:30 | Juan Pablo Varillas v Federico Arnaboldi | 6-4,7-6 |
| Challenger Sanremo | 2023/03/27 09:55 | Federico Arnaboldi v Julian Ocleppo | 7-6,6-1 |
| Challenger Sanremo | 2023/03/26 13:10 | Alexander Ritschard v Federico Arnaboldi | 4-6,3-6 |