Stadium: Cancha Central Round: 26 Ground: Clay
| Challenger Lima | 2016/10/24 21:25 | Jordi Samper-Montana v Leonardo Mayer | 3-6,4-6 |
| Challenger Santiago 2 | 2016/10/19 18:45 | Maximo Gonzalez v Leonardo Mayer | 6-1,6-2 |
| Challenger Santiago 2 | 2016/10/18 16:55 | Tomas Barrios Vera v Leonardo Mayer | 4-6,4-6 |
| Challenger Buenos Aires 2 | 2016/10/16 20:25 | Leonardo Mayer v Renzo Olivo | 6-2,6-7,6-7 |
| Challenger Buenos Aires 2 | 2016/10/15 21:45 | Rogerio Dutra Silva v Leonardo Mayer | 3-6,6-7 |
| Challenger Buenos Aires 2 | 2016/10/14 15:00 | Thiago Monteiro v Leonardo Mayer | 2-6,3-6 |
| Challenger Buenos Aires 2 | 2016/10/13 18:05 | Facundo Mena v Leonardo Mayer | 3-6,6-4,4-6 |
| Challenger Buenos Aires 2 | 2016/10/12 00:30 | Gabriel Alejandro Hidalgo v Leonardo Mayer | 3-6,1-6 |
| French Open | 2016/05/22 11:45 | Kei Nishikori v Simone Bolelli | 6-1,7-5,6-3 |
| ATP Marrakech | 2016/04/05 13:50 | Simone Bolelli v Taro Daniel | 7-5,6-4 |
| ATP Miami | 2016/03/23 22:50 | Taylor Fritz v Simone Bolelli | 6-4,6-2 |
| Challenger Shanghai | 2015/10/13 05:30 | Simone Bolelli v Vasek Pospisil | 3-6,4-6 |
| Challenger Shanghai | 2015/10/10 04:00 | Simone Bolelli v Matteo Donati | 6-4,6-3 |
| Davis Cup | 2015/09/18 07:00 | Teymuraz Gabashvili v Simone Bolelli | 7-6,6-1,6-3 |
| US Open | 2015/08/31 15:00 | Simone Bolelli v David Goffin | 4-6,1-6,2-6 |
| Challenger Prague 2 | 2015/08/14 11:00 | Axel Michon v Simone Bolelli | 6-2,4-6,7-6 |