Stadium: Court 4 Round: 28 Ground: Clay
| ITF M25 Santa Margherita | 2023/09/26 13:20 | Goncalo Oliveira v Gabriele Piraino | 5-7,4-6 |
| ITF M25 Santa Margherita | 2023/04/11 12:00 | Gabriele Piraino v Goncalo Oliveira | 2-6,1-6 |
| ITF M25 Vila Real de Santo Antonio | 2023/02/10 09:30 | Gabriele Piraino v Goncalo Oliveira | 7-5,3-6,6-3 |
| ITF M25 Santa Margherita | 2023/10/05 08:55 | Goncalo Oliveira v Kilian Feldbausch | 6-3,3-6,6-2 |
| ITF M25 Santa Margherita | 2023/10/04 12:25 | Goncalo Oliveira v Federico Arnaboldi | 6-3,6-3 |
| ITF M25 Santa Margherita | 2023/10/02 10:40 | Goncalo Oliveira v Pietro Pampanin | 2-6,6-2,6-3 |
| ITF M25 Santa Margherita | 2023/09/26 13:20 | Goncalo Oliveira v Gabriele Piraino | 5-7,4-6 |
| 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 Santa Margherita | 2023/10/05 09:00 | Gabriele Piraino v Marcello Serafini | 6-3,2-6,6-3 |
| ITF M25 Santa Margherita | 2023/10/04 10:55 | Gabriele Piraino v Giannicola Misasi | 6-3,6-0 |
| ITF M25 Santa Margherita | 2023/10/02 12:00 | Lorenzo Rottoli v Gabriele Piraino | 6-4,2-6,4-6 |
| ITF M25 Santa Margherita | 2023/09/27 10:55 | Gabriele Piraino v Luca Potenza | 1-6,6-2,3-6 |
| ITF M25 Santa Margherita | 2023/09/26 13:20 | Goncalo Oliveira v Gabriele Piraino | 5-7,4-6 |
| 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 |