Stadium: Cancha Estadio Round: 28 Ground: Clay
| Challenger Medellin | 2023/06/29 15:00 | Patrick Kypson v Matias Soto | 6-3,6-2 |
| Challenger Medellin | 2023/06/28 15:00 | Patrick Kypson v Gonzalo Lama | 7-6,6-1 |
| Challenger Medellin | 2023/06/27 16:40 | Patrick Kypson v Matias Franco Descotte | 6-4,6-3 |
| Challenger Cali | 2023/06/20 18:15 | Pedro Sakamoto v Patrick Kypson | 7-5,6-3 |
| Challenger Palmas del Mar | 2023/06/13 15:00 | Patrick Kypson v Alexis Galarneau | 3-6,0-6 |
| Challenger Tyler | 2023/06/04 17:25 | Patrick Kypson v Rubin Statham | 6-7,6-4,6-7 |
| French Open | 2023/05/28 09:00 | Patrick Kypson v Radu Albot | 3-6,2-6,6-4,1-6 |
| Challenger - Savannah | 2023/04/29 17:30 | Patrick Kypson v Facundo Diaz Acosta | 3-6,6-4,4-6 |
| Challenger Medellin | 2023/06/29 16:15 | Eduardo Ribeiro v Santiago Rodriguez Taverna | 6-3,4-6,6-2 |
| Challenger Medellin | 2023/06/28 15:00 | Eduardo Ribeiro v Gerald Melzer | 6-3,6-4 |
| Challenger Medellin | 2023/06/27 15:00 | Tristan Schoolkate v Eduardo Ribeiro | 2-6,6-7 |
| Challenger Cali | 2023/06/20 16:00 | Eduardo Ribeiro v Federico Delbonis | 2-6,3-6 |
| Challenger Vicenza | 2023/05/29 10:40 | Eduardo Ribeiro v Nino Serdarusic | 1-6,2-6 |
| Challenger Vicenza | 2023/05/28 12:15 | Salvatore Caruso v Eduardo Ribeiro | 2-6,3-6 |
| Challenger Skopje | 2023/05/22 10:30 | Eduardo Ribeiro v Steven Diez | 6-4,0-6,3-6 |
| Challenger Oeiras | 2023/05/16 09:00 | Pedro Cachin v Eduardo Ribeiro | 5-7,7-6,6-3 |