Stadium: Center Court Round: 28 Ground: Clay
| Challenger Santiago 2 | 2016/10/20 18:00 | Horacio Zeballos v Pedro Sousa | 7-6,6-4 |
| Challenger Santiago 2 | 2016/10/19 21:10 | Pedro Sousa v Guido Andreozzi | 7-5,7-5 |
| Challenger Santiago 2 | 2016/10/18 16:50 | Tomas Lipovsek Puches v Pedro Sousa | 5-7,6-3,3-6 |
| Challenger Buenos Aires 2 | 2016/10/14 18:40 | Renzo Olivo v Pedro Sousa | 6-2,6-3 |
| Challenger Buenos Aires 2 | 2016/10/13 20:20 | Pedro Sousa v Juan Pablo Paz | 7-5,7-5 |
| Challenger Buenos Aires 2 | 2016/10/11 19:40 | Marcelo Zormann v Pedro Sousa | 1-6,4-6 |
| Challenger Campinas | 2016/10/08 18:30 | Carlos Berlocq v Pedro Sousa | 6-0,6-4 |
| Challenger Campinas | 2016/10/07 16:40 | Juan Ignacio Londero v Pedro Sousa | 5-7,6-7 |
| ATP Chennai Qual | 2016/12/31 11:40 | Yuki Bhambri v Marco Cecchinato | 7-5,6-1 |
| ATP Stockholm Qual | 2016/10/15 09:05 | Matthias Bachinger v Marco Cecchinato | 7-6,6-2 |
| Challenger Rome 2 | 2016/09/26 15:20 | Marco Cecchinato v Aljaz Bedene | 1-6,1-6 |
| Challenger Szczecin | 2016/09/16 12:30 | Jonathan Eysseric v Marco Cecchinato | 6-4,6-1 |
| Challenger Szczecin | 2016/09/15 15:00 | Casper Ruud v Marco Cecchinato | 7-5,1-6,2-6 |
| Challenger Szczecin | 2016/09/13 11:10 | Boy Westerhof v Marco Cecchinato | 4-6,1-6 |
| Challenger Genova | 2016/09/08 13:40 | Marco Cecchinato v Adam Pavlasek | 6-2,4-6,2-6 |
| Challenger Genova | 2016/09/07 14:55 | Steven Diez v Marco Cecchinato | 4-6,6-7 |