Round: 26 Ground: Clay
| Challenger Barranquilla | 2016/09/07 19:55 | Giraldo, Santiago v Hocevar, Ricardo | 6-0,6-2 |
| 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 |
| Challenger Barranquilla | 2016/09/06 20:00 | Cordonnier, Gregorio v Falla, Alejandro | 4-6,1-6 |
| ATP Washington Qual | 2016/07/16 15:20 | Mackenzie McDonald v Falla, Alejandro | 3-6,6-3,6-7 |
| ATP Newport Qual | 2016/07/10 16:00 | Falla, Alejandro v Daniel Cox | 3-6,4-6 |
| Wimbledon Qual | 2016/06/22 12:50 | Falla, Alejandro v Jozef Kovalik | 3-6,7-6,11-13 |
| Wimbledon Qual | 2016/06/21 09:30 | Falla, Alejandro v Salvatore Caruso | 7-6,6-1 |
| French Open Qual | 2016/05/16 15:20 | Falla, Alejandro v Berlocq, Carlos | 4-6,4-6 |
| Challenger - Bordeaux | 2016/05/12 15:30 | Dutra Silva, Rogerio v Falla, Alejandro | 6-1,6-2 |
| Challenger - Bordeaux | 2016/05/10 13:30 | Falla, Alejandro v Calvin Hemery | 6-2,6-0 |