Stadium: Serena Maniva Centre Round: 26 Ground: Clay
| Challenger - Cordenons | 2023/08/08 08:00 | Carlos Taberner v Blaz Rola | 6-2,1-6,4-6 |
| Challenger - Triëst | 2023/07/16 16:15 | Blaz Rola v Kirill Kivattsev | 6-4,4-6,4-6 |
| Challenger - Salzburg | 2023/07/15 11:00 | Blaz Rola v Lukas Neumayer | 4-6,6-3,5-7 |
| Challenger - Salzburg | 2023/07/14 10:30 | Blaz Rola v Filip Misolic | 6-3,6-3 |
| Challenger - Salzburg | 2023/07/13 09:30 | Blaz Rola v Vit Kopriva | 6-3,1-6,6-3 |
| Challenger - Salzburg | 2023/07/11 13:15 | Roberto Carballes Baena v Blaz Rola | 6-7,1-6 |
| Challenger - Salzburg | 2023/07/10 10:30 | Guido Andreozzi v Blaz Rola | 6-3,4-6,4-6 |
| Challenger - Salzburg | 2023/07/09 12:55 | Roko Horvat v Blaz Rola | 1-6,0-6 |
| Challenger - Cordenons | 2023/08/08 17:30 | Vladyslav Orlov v Matteo Gigante | 7-6,4-6,4-6 |
| Challenger Zug | 2023/07/28 13:00 | Matteo Gigante v Joris De Loore | 6-3,6-7,4-6 |
| Challenger Zug | 2023/07/27 08:30 | Dimitar Kuzmanov v Matteo Gigante | 4-6,6-7 |
| Challenger Zug | 2023/07/26 13:45 | Dalibor Svrcina v Matteo Gigante | 1-6,7-6,3-6 |
| Challenger - Triëst | 2023/07/19 14:45 | Fabian Marozsan v Matteo Gigante | 7-6,3-6,7-5 |
| Challenger - Triëst | 2023/07/18 08:00 | Clement Tabur v Matteo Gigante | 4-6,7-6,3-6 |
| Challenger - San Benedetto | 2023/07/11 13:50 | Michael Geerts v Matteo Gigante | 4-6,6-4,6-4 |
| Challenger - Milaan | 2023/07/09 14:30 | Facundo Diaz Acosta v Matteo Gigante | 6-3,6-3 |