Stadium: Court 2 Round: 26 Ground: Clay
| ITF Peru F3 | 2018/10/12 16:00 | Gonzalo Villanueva v Mariano Kestelboim | 5-7,7-6,3-6 |
| ITF Argentina F9 | 2017/11/15 16:40 | Mariano Kestelboim v Gonzalo Villanueva | 6-3,2-6,7-6 |
| ITF Argentina F5 | 2016/05/03 18:00 | Gonzalo Villanueva v Mariano Kestelboim | 4-6,4-6 |
| ITF Argentina F3 | 2015/03/24 14:50 | Mariano Kestelboim v Gonzalo Villanueva | 6-4,0-6,3-6 |
| ITF M25 Punta del Este | 2020/02/18 17:30 | Alejo Vilaro v Mariano Kestelboim | 2-6,6-4,2-6 |
| ITF M25 Lima | 2020/02/15 15:00 | Tomas Barrios Vera v Mariano Kestelboim | 6-3,4-6,7-5 |
| ITF M25 Lima | 2020/02/14 16:00 | Federico Zeballos v Mariano Kestelboim | 2-6,1-6 |
| ITF M25 Lima | 2020/02/13 18:15 | Mariano Kestelboim v Thiago Agustin Tirante | 5-7,7-6,6-4 |
| ITF M25 Lima | 2020/02/11 15:00 | Rafael Matos v Mariano Kestelboim | 5-7,6-4,2-6 |
| ITF M25 Lima | 2020/02/06 14:55 | Tomas Barrios Vera v Mariano Kestelboim | 6-4,6-3 |
| ITF M25 Lima | 2020/02/05 14:50 | Mariano Kestelboim v Rafael Matos | 6-4,6-3 |
| ITF M25 Lima | 2020/02/03 16:35 | Mariano Kestelboim v Alejandro Mendoza | 6-0,6-0 |
| ITF M25 Punta del Este | 2020/02/18 19:35 | Agustin Riquelme Coppari v Gonzalo Villanueva | 1-6,1-6 |
| ITF M25 Lima | 2020/02/14 17:25 | Pedro Sakamoto v Gonzalo Villanueva | 6-3,6-4 |
| ITF M25 Lima | 2020/02/11 17:00 | Gonzalo Bueno v Gonzalo Villanueva | 2-6,1-6 |
| ITF M25 Lima | 2020/02/05 14:30 | Tomas Barrios Vera v Gonzalo Villanueva | 6-3,6-3 |
| Challenger Punta del Este | 2020/01/29 22:00 | Marco Cecchinato v Gonzalo Villanueva | 6-0,6-3 |
| Challenger Punta del Este | 2020/01/28 00:10 | Gonzalo Villanueva v Juan Martin Fumeaux | 6-2,6-0 |
| ITF M25 Naples | 2019/11/19 19:00 | Gonzalo Villanueva v Roberto Cid Subervi | 6-4,0-6,3-6 |
| Challenger Houston | 2019/11/14 00:35 | Gonzalo Villanueva v Jenson Brooksby | 2-6,2-6 |