Round: 25 Ground: Clay
| US Open, New York, USA, Qualifying | 2016/08/26 18:10 | Donaldson, Jared v Giraldo, Santiago | 6-2,6-2 |
| US Open, New York, USA, Qualifying | 2016/08/24 20:50 | Arevalo-Gonzalez, Marcelo v Giraldo, Santiago | 6-7,6-7 |
| Challenger Prague 2 | 2016/07/31 11:00 | Giraldo, Santiago v Ignatik, Uladzimir | 6-4,3-6,7-6 |
| Challenger Prague 2 | 2016/07/30 13:00 | Giraldo, Santiago v Zdenek Kolar | 6-4,6-4 |
| Challenger Prague 2 | 2016/07/29 15:00 | Martin Klizan v Giraldo, Santiago | 1-6,5-7 |
| Challenger Prague 2 | 2016/07/28 10:00 | Hubert Hurkacz v Giraldo, Santiago | 3-6,1-6 |
| Challenger Prague 2 | 2016/07/25 09:00 | Mertl, Jan v Giraldo, Santiago | 5-7,6-7 |
| Coupe Davis | 2016/07/16 14:00 | Nicolas Jarry v Giraldo, Santiago | 2-6,4-6,3-6 |
| Challenger Curitiba | 2016/08/31 14:00 | Hocevar, Ricardo v Santanna, B. | 6-7,3-6 |
| ITF Brazil F4 | 2016/07/22 15:05 | Hocevar, Ricardo v Telles, Leonardo | 4-6,4-6 |
| ITF Brazil F4 | 2016/07/21 14:00 | Hocevar, Ricardo v Kohen, Alan | 6-2,6-1 |
| ITF Brazil F4 | 2016/07/19 14:25 | Hocevar, Ricardo v Bertucci, Federico Nicolas | 7-6,6-2 |
| ITF Brazil F3 | 2016/07/17 13:00 | Hidalgo, Gabriel Alejandro v Hocevar, Ricardo | 6-3,6-4 |
| ITF Brazil F3 | 2016/07/16 19:15 | Hocevar, Ricardo v Ribeiro Marcondes, Igor | 6-4,6-3 |
| ITF Brazil F3 | 2016/07/15 20:15 | Gasperini, Lourenzo v Hocevar, Ricardo | 5-7,2-6 |
| ITF Brazil F3 | 2016/07/13 16:35 | Laranja, Augusto v Hocevar, Ricardo | 4-6,0-6 |