Stadium: Court 2 Round: 26 Ground: Clay
| ITF M15 Sharm El Sheikh | 2023/02/15 12:30 | Gabriele Pennaforti v Gabriele Bosio | 6-4,6-2 |
| ITF M25 Idanha-A-Nova | 2023/08/24 11:35 | Gabriele Bosio v Arthur Fery | 7-5,2-6,2-6 |
| ITF M25 Idanha-A-Nova | 2023/08/22 08:00 | Gabriele Bosio v Duarte Vale | 7-5,6-1 |
| ITF M15 Kottingbrunn | 2023/08/18 08:00 | Gabriele Bosio v Matej Dodig | 7-6,4-6,4-6 |
| ITF M15 Kottingbrunn | 2023/08/17 10:40 | Mohamed Safwat v Gabriele Bosio | 6-2,4-6,2-6 |
| ITF M15 Kottingbrunn | 2023/08/16 08:00 | Gabriele Bosio v Jan Kobierski | 6-3,3-6,6-4 |
| ITF M15 Monastir | 2023/07/26 10:00 | Matthew William Donald v Gabriele Bosio | 4-6,6-2,6-3 |
| ITF M15 Monastir | 2023/07/19 09:30 | Cyril Vandermeersch v Gabriele Bosio | 6-2,6-2 |
| ITF M15 Monastir | 2023/07/16 08:00 | Gabriele Bosio v Sandro Cottino | 6-3,6-4 |
| ITF M15 Forli | 2023/08/28 16:15 | Lorenzo Beraldo v Gabriele Pennaforti | 2-6,3-6 |
| ITF M25 Lesa | 2023/08/23 12:25 | Gabriele Pennaforti v Timo Legout | 2-6,4-6 |
| Challenger Todi | 2023/08/14 10:40 | Giovanni Oradini v Gabriele Pennaforti | 7-6,2-6,6-3 |
| ITF M15 Curtea de Arges | 2023/08/12 10:10 | Gabriele Pennaforti v Gabi Adrian Boitan | 4-6,1-6 |
| ITF M15 Curtea de Arges | 2023/08/11 10:25 | Gabriele Pennaforti v Luciano Emanuel Ambrogi | 6-4,6-2 |
| ITF M15 Curtea de Arges | 2023/08/10 14:10 | Gabriele Pennaforti v Calin Manda | 2-6,6-3,6-3 |
| ITF M15 Curtea de Arges | 2023/08/09 12:25 | Gabriele Pennaforti v Nicolas Bruna | 2-6,6-2,6-4 |
| ITF M15 Hyvinkaa | 2023/08/04 12:15 | Maxence Rivet v Gabriele Pennaforti | 6-0,6-7,6-4 |