Stadium: Centre Court Round: 19 Ground: Clay
| Challenger Todi | 2023/08/13 14:00 | Giovanni Oradini v Alessio De Bernardis | 6-3,6-0 |
| Challenger Cordenons | 2023/08/07 13:15 | Giovanni Oradini v Juan Bautista Otegui | 2-6,2-6 |
| Challenger Cordenons | 2023/08/07 09:00 | Giovanni Oradini v Bor Artnak | 7-6,6-3 |
| ITF M25 Bolzano | 2023/08/05 08:55 | Mathys Erhard v Giovanni Oradini | 6-4,3-6,6-7 |
| ITF M25 Bolzano | 2023/08/04 08:30 | Giovanni Oradini v Alex Barrena | 6-3,6-4 |
| ITF M25 Bolzano | 2023/08/03 11:25 | Jeremy Jahn v Giovanni Oradini | 3-6,1-6 |
| ITF M25 Bolzano | 2023/08/02 11:00 | Samuele Pieri v Giovanni Oradini | 1-6,1-6 |
| ITF M25 Bolzano | 2023/08/01 10:35 | Antonio Caruso v Giovanni Oradini | 4-6,0-6 |
| 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 |
| ITF M15 Hyvinkaa | 2023/08/03 06:30 | Patrick Kaukovalta v Gabriele Pennaforti | 2-6,7-6,3-6 |
| Challenger Verona | 2023/07/23 09:20 | Gabriele Pennaforti v Francesco Forti | 7-6,4-6,6-7 |
| ITF M25 Padova | 2023/07/15 14:30 | Samuel Vincent Ruggeri v Gabriele Pennaforti | 6-2,6-3 |