Stadium: Court Esperance Banlieues Round: 25 Ground: Clay
| Challenger Santiago 2 | 2016/10/20 19:50 | Axel Michon v Thiago Monteiro | 5-7,4-6 |
| Challenger Santiago 2 | 2016/10/19 17:00 | Juan Pablo Paz v Thiago Monteiro | 4-6,2-6 |
| Challenger Santiago 2 | 2016/10/18 18:40 | Juan Ignacio Londero v Thiago Monteiro | 5-7,6-7 |
| Challenger Buenos Aires 2 | 2016/10/14 15:00 | Thiago Monteiro v Leonardo Mayer | 2-6,3-6 |
| Challenger Buenos Aires 2 | 2016/10/12 16:25 | Thiago Monteiro v Maximo Gonzalez | 4-6,6-3,6-2 |
| Challenger Buenos Aires 2 | 2016/10/11 17:40 | Thiago Monteiro v Axel Michon | 7-6,2-6,7-6 |
| Challenger Campinas | 2016/10/07 22:50 | Rogerio Dutra Silva v Thiago Monteiro | 6-3,4-6,6-1 |
| Challenger Campinas | 2016/10/06 20:20 | Andrea Collarini v Thiago Monteiro | 6-7,4-6 |
| ATP Antwerp | 2016/10/22 12:00 | Richard Gasquet v Kyle Edmund | 3-6,7-5,6-2 |
| ATP Antwerp | 2016/10/21 16:50 | Andreas Seppi v Kyle Edmund | 3-6,4-6 |
| ATP Antwerp | 2016/10/20 16:45 | Kyle Edmund v David Ferrer | 6-1,3-6,7-6 |
| ATP Antwerp | 2016/10/18 14:00 | Kyle Edmund v Illya Marchenko | 7-6,7-6 |
| ATP Shanghai | 2016/10/12 05:00 | Kyle Edmund v Stan Wawrinka | 3-6,4-6 |
| ATP Shanghai | 2016/10/10 06:25 | Kyle Edmund v Federico Delbonis | 6-3,5-7,6-4 |
| ATP Shanghai Qual | 2016/10/09 07:45 | Kyle Edmund v Dusan Lajovic | 6-4,2-6,6-3 |
| ATP Shanghai Qual | 2016/10/08 08:00 | Kyle Edmund v Yecong He | 6-3,6-2 |