Stadium: Court 1 Round: 25 Ground: Clay
| ITF - M25 Santa Margherita | 2023/09/25 08:00 | Sander Jong v Gian M Di Natale | 6-3,6-4 |
| ITF - M25 Santa Margherita | 2023/09/24 08:00 | Sander Jong v Paolo Schiavone | 6-1,6-0 |
| ITF - M25 Santa Margherita | 2023/09/18 13:00 | Sander Jong v Luigi Sorrentino | 6-3,3-6,4-6 |
| ITF - M15 Haren | 2023/09/08 14:10 | Sidane Pontjodikromo v Sander Jong | 6-4,6-1 |
| ITF - M15 Haren | 2023/09/07 10:50 | David Fix v Sander Jong | 4-6,1-6 |
| ITF - M15 Haren | 2023/09/06 12:40 | Stijn Slump v Sander Jong | 6-7,7-6,4-6 |
| ITF - M25 Oldenzaal | 2023/08/31 10:25 | Sander Jong v Lucas Gerch | 2-6,6-7 |
| ITF - M25 Oldenzaal | 2023/08/30 17:25 | Sander Jong v Twan Van Zijl | 7-5,6-0 |
| ITF - M25 Santa Margherita | 2023/09/25 08:00 | Gabriele Pennaforti v Giuseppe La Vela | 6-4,6-0 |
| ITF - M25 Santa Margherita | 2023/09/24 08:00 | Gabriele Pennaforti v Biagio Gramaticopolo | 6-1,6-4 |
| ITF - M15 Kuršumlijska Banja | 2023/09/15 09:50 | Francesco Ferrari v Gabriele Pennaforti | 6-3,5-7,6-3 |
| ITF - M15 Kuršumlijska Banja | 2023/09/14 08:00 | Sasa Markovic v Gabriele Pennaforti | 4-6,4-6 |
| ITF - M15 Kuršumlijska Banja | 2023/09/13 13:00 | Zoran Ludoski v Gabriele Pennaforti | 3-6,4-6 |
| Challenger - Janov | 2023/09/03 14:05 | Gabriele Pennaforti v Lorenzo Rottoli | 4-6,6-2,1-6 |
| ITF - M15 Forli | 2023/09/02 08:45 | Gabriele Pennaforti v Giorgio Tabacco | 6-4,6-2 |
| ITF - M15 Forli | 2023/09/01 14:05 | Gabriele Pennaforti v Daniel Bagnolini | 6-3,6-1 |