Stadium: Court 3 Round: 14 Ground: Clay
| Challenger Quito | 2021/09/14 15:00 | Gonzalo Villanueva v Renzo Olivo | 4-6,4-6 |
| Challenger Tulln | 2021/09/06 08:00 | Neil Oberleitner v Gonzalo Villanueva | 7-5,6-2 |
| Challenger Tulln | 2021/09/05 10:40 | Pavel Nejedly v Gonzalo Villanueva | 2-6,4-6 |
| ITF M15 Zilina | 2021/09/01 12:25 | Gonzalo Villanueva v Peter Goldsteiner | 4-6,3-6 |
| ITF M25 Decatur | 2021/08/04 20:30 | Gonzalo Villanueva v Petros Chrysochos | 1-6,3-6 |
| Challenger Lexington | 2021/07/25 17:00 | Aidan Mchugh v Gonzalo Villanueva | 7-5,2-6,6-3 |
| Challenger Cary | 2021/07/20 15:00 | Roberto Cid Subervi v Gonzalo Villanueva | 3-6,7-5,6-1 |
| UTR Pro Tennis Series Atlanta | 2021/07/16 12:00 | Ivan Yatsuk v Gonzalo Villanueva | 6-1,6-4 |
| Challenger Quito | 2021/09/14 19:35 | Alejandro Gonzalez v Luca Castelnuovo | 6-2,7-6 |
| Challenger Quito | 2021/09/13 16:20 | Luca Castelnuovo v Hugo Minda | 6-4,6-3 |
| ITF M25 Sierre | 2021/09/03 10:00 | Rinky Hijikata v Luca Castelnuovo | 6-3,3-6,7-5 |
| ITF M25 Sierre | 2021/09/02 07:55 | Luca Castelnuovo v Moez Echargui | 7-6,7-6 |
| ITF M25 Sierre | 2021/08/31 16:30 | Luca Castelnuovo v Gian Luca Tanner | 7-5,6-3 |
| ITF M25 Muttenz | 2021/08/19 10:35 | Luca Castelnuovo v Oscar Jose Gutierrez | 1-6,2-6 |
| ITF M25 Muttenz | 2021/08/18 12:50 | Gabriele Moghini v Luca Castelnuovo | 6-7,1-6 |
| Challenger Tampere | 2021/07/18 10:20 | Kyrian Jacquet v Luca Castelnuovo | 6-7,6-1,6-0 |