Stadion: Court 3 Round: 25 Ground: Clay
| ITF - M25 - Santa Margherita | 2023/04/11 12:00 | Gabriele Piraino v Goncalo Oliveira | 2-6,1-6 |
| ITF - M25 - Vila Real de Santo António | 2023/02/10 09:30 | Gabriele Piraino v Goncalo Oliveira | 7-5,3-6,6-3 |
| ITF - M25 - Sintra | 2023/09/15 10:50 | Goncalo Oliveira v Tiago Pereira | 6-4,3-6,6-2 |
| ITF - M25 - Sintra | 2023/09/14 10:40 | Goncalo Oliveira v Francisco Rocha | 6-3,6-2 |
| ITF - M25 - Sintra | 2023/09/13 09:00 | Goncalo Oliveira v Leopold Zima | 6-0,6-1 |
| ITF - M25 - Idanha-A-Nova | 2023/09/04 08:00 | Goncalo Oliveira v Alberto Barroso Campos | 6-4,6-4 |
| ITF - M25 - Idanha-A-Nova | 2023/09/02 08:00 | Goncalo Oliveira v Robin Bertrand | 4-6,6-3,6-4 |
| ITF - M25 - Idanha-A-Nova | 2023/09/01 08:00 | Goncalo Oliveira v Loic N Tenguere | 6-2,6-4 |
| ITF - M25 - Idanha-A-Nova | 2023/08/31 10:15 | Goncalo Oliveira v Goncalo Marques | 6-3,6-3 |
| ITF - M25 - Idanha-A-Nova | 2023/08/30 08:00 | Goncalo Oliveira v Alexander Bravo | 6-1,6-1 |
| ITF - M25 - Santa Margherita | 2023/09/22 11:00 | Daniel Michalski v Gabriele Piraino | 6-1,6-2 |
| ITF - M25 - Santa Margherita | 2023/09/21 08:30 | Gabriele Piraino v Giuseppe La Vela | 6-3,6-1 |
| ITF - M25 - Santa Margherita | 2023/09/20 14:25 | Gabriele Piraino v Luigi Sorrentino | 1-6,6-3,7-5 |
| ITF - M25 - Santa Margherita | 2023/09/18 12:55 | Gabriele Piraino v Niccolo Ciavarella | 6-4,6-1 |
| Challenger - Genua | 2023/09/03 11:15 | Luca Castagnola v Gabriele Piraino | 6-3,5-7,6-1 |
| ITF - M15 - Forli | 2023/08/30 09:55 | Luigi Sorrentino v Gabriele Piraino | 6-3,6-2 |
| ITF - M15 - Forli | 2023/08/28 14:20 | Alexandr Binda v Gabriele Piraino | 1-6,4-6 |
| Challenger - Prag | 2023/08/20 11:10 | Niki Kaliyanda Poonacha v Gabriele Piraino | 7-5,6-3 |