Stadium: Cancha Central Round: 25 Ground: Clay
| Challenger Guayaquil | 2023/10/31 19:00 | Franco Agamenone v Oliver Crawford | 6-3,4-6,6-1 |
| Challenger Curitiba | 2023/10/29 18:00 | Hugo Dellien v Oliver Crawford | 7-6,4-6,7-6 |
| Challenger Curitiba | 2023/10/29 13:00 | Luciano Darderi v Oliver Crawford | 2-6,3-6 |
| Challenger Curitiba | 2023/10/28 15:20 | Oliver Crawford v Dalibor Svrcina | 7-6,2-6,6-1 |
| Challenger Curitiba | 2023/10/27 20:00 | Felipe Meligeni Rodrigues Alves v Oliver Crawford | 6-3,5-7,4-6 |
| Challenger Curitiba | 2023/10/24 19:25 | Oliver Crawford v Juan Bautista Torres | 6-1,6-3 |
| Challenger Charleston | 2023/10/01 15:00 | Oliver Crawford v Abedallah Shelbayh | 2-6,7-6,3-6 |
| Challenger Charleston | 2023/09/29 15:00 | Oliver Crawford v Stefan Dostanic | 6-1,6-2 |
| Challenger Guayaquil | 2023/10/29 19:25 | Arklon H D Pino v Mateus Alves | 1-6,4-6 |
| Challenger Curitiba | 2023/10/24 13:00 | Joao Lucas Reis da Silva v Arklon H D Pino | 6-4,6-4 |
| Challenger Curitiba | 2023/10/23 15:35 | Vitek Horak v Arklon H D Pino | 2-6,2-6 |
| Challenger Curitiba | 2023/10/22 19:20 | Arklon H D Pino v Alafia Ayeni | 7-5,6-4 |
| ITF M25 Lajeado | 2023/10/13 20:00 | Wilson Leite v Arklon H D Pino | 7-6,6-2 |
| ITF M25 Lajeado | 2023/10/13 13:55 | Arklon H D Pino v Ezequiel Simonit | 7-5,6-7,6-1 |
| ITF M25 Lajeado | 2023/10/12 15:45 | Arklon H D Pino v Luis Britto | 3-6,6-4,6-0 |
| ITF M25 Mendoza | 2023/10/07 17:00 | Arklon H D Pino v Ignacio Buse | 1-6,4-6 |