Estadio: Court 3 Round: 26 Ground: Hardcourt outdoor
| ITF M25 Santo Domingo | 2023/02/22 19:25 | Preston Brown v Cash Hanzlik | 6-4,6-1 |
| ITF M25 Santo Domingo | 2023/02/15 16:55 | Preston Brown v Jesse Flores | 2-6,2-6 |
| ITF M25 Santo Domingo | 2023/02/14 13:00 | Preston Brown v Christian Heaney-Secord | 6-1,7-5 |
| ITF M25 Santo Domingo | 2023/02/13 17:00 | Preston Brown v Emilio Andrea Segarelli | 6-2,7-5 |
| ITF M15 Edmond | 2023/01/25 16:00 | Preston Brown v Marko Mesarovic | 4-6,4-6 |
| Challenger de Nouméa | 2023/01/02 00:00 | Blake Ellis v Preston Brown | 1-6,7-5,6-1 |
| Challenger de Nouméa | 2023/01/01 01:25 | Tiago Lopes v Preston Brown | 1-6,1-6 |
| ITF M15 Tauranga | 2022/12/20 01:00 | Preston Brown v Isaac Becroft | 2-6,4-6 |
| ITF M25 Santo Domingo | 2023/02/21 16:30 | Nicholas Godsick v Gonzalo Villanueva | 6-3,2-6,3-6 |
| ITF M25 Santo Domingo | 2023/02/17 15:45 | Kyle Seelig v Gonzalo Villanueva | 6-2,6-1 |
| ITF M25 Santo Domingo | 2023/02/16 16:45 | Ezekiel Clark v Gonzalo Villanueva | 3-6,6-1,2-6 |
| ITF M25 Santo Domingo | 2023/02/15 15:40 | Nicholas Godsick v Gonzalo Villanueva | 6-3,4-6,5-7 |
| Challenger de Concepción | 2023/01/22 18:20 | Thiago Seyboth Wild v Gonzalo Villanueva | 6-3,7-6 |
| Challenger de Piracicaba | 2023/01/16 13:00 | Gonzalo Villanueva v Edoardo Lavagno | 4-6,4-6 |
| Challenger de Piracicaba | 2023/01/15 15:05 | Gonzalo Villanueva v Matheus C Bueres | 6-2,6-0 |
| Challenger de Tigre | 2023/01/13 17:50 | Jesper De Jong v Gonzalo Villanueva | 6-2,7-6 |