Stadium: Cancha 2 Round: 25 Ground: Clay
| Challenger Tigre | 2023/01/07 16:05 | Murkel Dellien v Gonzalo Villanueva | 6-4,6-0 |
| Challenger Tigre | 2023/01/06 13:00 | Gonzalo Villanueva v Valerio Aboian | 7-5,6-7,6-4 |
| Challenger Tigre | 2023/01/05 15:15 | Gonzalo Villanueva v Remy Bertola | 6-2,6-3 |
| Challenger Tigre | 2023/01/04 14:55 | Oriol Roca Batalla v Gonzalo Villanueva | 2-6,6-2,3-6 |
| Challenger Temuco | 2022/11/22 19:30 | Tomas Farjat v Gonzalo Villanueva | 6-3,6-4 |
| Challenger Sao Leopoldo | 2022/11/15 16:30 | Gonzalo Villanueva v Facundo Diaz Acosta | 3-6,3-6 |
| Challenger Montevideo | 2022/11/08 20:45 | Gonzalo Villanueva v Juan Pablo Paz | 4-6,6-7 |
| Challenger Montevideo | 2022/11/07 18:40 | Gonzalo Villanueva v Federico Zeballos | 3-6,4-6 |
| Challenger Tigre | 2023/01/03 19:05 | Daniel Dutra Da Silva v Evan Zhu | 7-6,6-2 |
| Challenger Champaign | 2022/11/18 19:50 | Christopher Eubanks v Evan Zhu | 6-1,6-2 |
| Challenger Champaign | 2022/11/16 20:15 | Evan Zhu v Strong Kirchheimer | 6-4,7-6 |
| Challenger Champaign | 2022/11/15 18:05 | Alexander Petrov v Evan Zhu | 0-6,4-6 |
| Challenger Champaign | 2022/11/14 17:15 | Evan Zhu v Patrick Kypson | 6-7,3-6 |
| Challenger Champaign | 2022/11/13 19:15 | Evan Zhu v Toby Alex Kodat | 6-3,7-6 |
| Challenger Calgary | 2022/11/09 02:15 | Evan Zhu v Vasek Pospisil | 3-6,4-6 |
| Challenger Las Vegas | 2022/10/27 18:00 | Evan Zhu v Stefan Kozlov | 6-7,2-6 |