Stadium: INDOOR 2 Round: 25 Ground: Clay
| ITF M25 Sintra | 2023/09/13 09:00 | Telles, Leonardo v Martin Damm | 3-6,2-6 |
| ITF M25 Sintra | 2023/09/12 09:00 | Diogo Marques v Telles, Leonardo | 6-4,4-6,8-10 |
| ITF M25 Sintra | 2023/09/11 13:00 | Telles, Leonardo v Antonio, Joao | 6-1,6-3 |
| ITF M25 Sintra | 2023/09/11 09:00 | Telles, Leonardo v Paschetto, Francesco | 6-4,6-2 |
| ITF M25 Sintra | 2023/09/06 08:30 | Lerby, Christian v Telles, Leonardo | 4-6,7-5,10-7 |
| ITF M25 Sintra | 2023/09/05 14:30 | Mackinlay, James v Telles, Leonardo | 1-6,0-6 |
| ITF M25 Sintra | 2023/09/03 08:00 | Telles, Leonardo v Ian Luca Cervantes Tomas | 6-1,6-4 |
| ITF M15 Cancun | 2021/10/03 19:45 | Leiva Biason, Oscar Mattias v Telles, Leonardo | 3-6,2-6 |
| ITF M25 Lajeado | 2023/10/10 12:55 | Pini, Francisco v Ryan A Dos Santos | 6-2,5-7,15-13 |
| ITF M25 Lajeado | 2023/10/09 16:00 | Pini, Francisco v Daniel V C Rebelo | 6-2,6-1 |
| ITF M15 Olavarria | 2023/09/05 14:50 | Bramajo, Santiago v Pini, Francisco | 6-0,6-2 |
| Buenos Aires, Singles Qualifying M-ITF-ARG-22A | 2023/09/01 14:40 | Bruno Kuzuhara v Pini, Francisco | 6-4,6-2 |
| Buenos Aires, Singles Qualifying M-ITF-ARG-22A | 2023/08/30 13:00 | Pini, Francisco v Leonardo Aboian | 4-6,6-4,6-3 |
| Buenos Aires, Singles Qualifying M-ITF-ARG-22A | 2023/08/29 13:00 | Vitor Leal v Pini, Francisco | 3-6,4-6 |
| Buenos Aires, Singles Qualifying M-ITF-ARG-22A | 2023/08/28 14:30 | Gonzalo Ariel Karakachian v Pini, Francisco | 6-4,2-6,4-10 |
| Buenos Aires, Singles Qualifying M-ITF-ARG-22A | 2023/08/27 16:00 | Pini, Francisco v Bramajo, Santiago | 6-3,2-6,11-9 |