Stadium: Cancha Central Round: 14 Ground: Clay
| Challenger Piracicaba | 2024/01/29 17:00 | Gonzalo Villanueva v Mariano Kestelboim | 6-2,7-5 |
| Challenger Piracicaba | 2024/01/29 13:00 | Gonzalo Villanueva v Fernando Yamacita | 6-2,6-0 |
| Challenger Buenos Aires | 2024/01/17 13:00 | Gonzalo Villanueva v Damien Wenger | 6-7,4-6 |
| Challenger Buenos Aires Qual | 2024/01/15 13:00 | Gonzalo Villanueva v Gerard Campana Lee | 6-4,7-6 |
| Challenger Buenos Aires Qual | 2024/01/14 15:55 | Gilbert S K Junior v Gonzalo Villanueva | 5-7,4-6 |
| Challenger Buenos Aires | 2024/01/09 20:05 | Oleksii Krutykh v Gonzalo Villanueva | 4-6,7-5,7-6 |
| Challenger Buenos Aires | 2024/01/08 15:15 | Adolfo Daniel Vallejo v Gonzalo Villanueva | 2-6,4-6 |
| Challenger Buenos Aires | 2024/01/07 13:00 | Vito Antonio Darderi v Gonzalo Villanueva | 1-6,0-6 |
| Challenger Cleveland | 2024/01/29 15:00 | Gabi Adrian Boitan v Felix Corwin | 6-3,6-4 |
| Challenger Cleveland | 2024/01/28 16:30 | Gabi Adrian Boitan v Sebastian Bielen | 6-4,6-0 |
| Challenger Champaign | 2023/11/12 16:00 | Gabi Adrian Boitan v Mark Whitehouse | 6-4,1-6,4-6 |
| Challenger Knoxville | 2023/11/06 18:00 | Cannon Kingsley v Gabi Adrian Boitan | 7-5,6-3 |
| Challenger Knoxville | 2023/11/05 22:00 | Alexander Kotzen v Gabi Adrian Boitan | 7-6,4-6,3-6 |
| Challenger Hamburg | 2023/10/15 08:00 | Gabi Adrian Boitan v Javier Barranco Cosano | 4-6,6-7 |
| Challenger Bratislava | 2023/10/10 09:00 | Andrew Paulson v Gabi Adrian Boitan | 6-4,6-3 |
| Challenger Bratislava | 2023/10/09 08:30 | Cem Ilkel v Gabi Adrian Boitan | 2-6,1-6 |