Stadium: MTA 05 Round: 62 Ground: Clay
| ITF M15 Santo Domingo | 2023/11/15 14:30 | Facundo Mena v Telles, Leonardo | 3-6,6-3,7-6 |
| ITF M15 Santo Domingo | 2023/11/14 13:00 | Telles, Leonardo v Jake Bhangdia | 6-1,6-1 |
| ITF M15 Santo Domingo | 2023/11/12 17:00 | Telles, Leonardo v Villanueva Quintana, Janio Antonio | 6-0,6-0 |
| ITF M15 Santo Domingo | 2023/11/10 13:00 | Roberto Cid Subervi v Telles, Leonardo | 6-4,6-1 |
| ITF M15 Santo Domingo | 2023/11/08 16:30 | Telles, Leonardo v Tim Ruehl | 6-0,5-7,6-3 |
| ITF - M25 Santo Domingo | 2023/11/07 13:00 | Telles, Leonardo v Stepan Mruzek | 6-4,6-0 |
| ITF - M25 Santo Domingo | 2023/11/06 13:30 | Telles, Leonardo v Diego I Munoz Gajardo | 6-1,6-0 |
| ITF - M15 Villa Maria | 2023/11/02 16:00 | Nicolas Bruna v Telles, Leonardo | 7-6,6-3 |