Round: 26 Ground: Clay
| Challenger Barranquilla | 2016/09/07 19:55 | Santiago Giraldo v Ricardo Hocevar | 6-0,6-2 |
| US Open Qual | 2016/08/26 18:10 | Jared Donaldson v Santiago Giraldo | 6-2,6-2 |
| US Open Qual | 2016/08/24 20:50 | Marcelo Arevalo v Santiago Giraldo | 6-7,6-7 |
| Challenger Prague 2 | 2016/07/31 11:00 | Santiago Giraldo v Uladzimir Ignatik | 6-4,3-6,7-6 |
| Challenger Prague 2 | 2016/07/30 13:00 | Santiago Giraldo v Zdenek Kolar | 6-4,6-4 |
| Challenger Prague 2 | 2016/07/29 15:00 | Martin Klizan v Santiago Giraldo | 1-6,5-7 |
| Challenger Prague 2 | 2016/07/28 10:00 | Hubert Hurkacz v Santiago Giraldo | 3-6,1-6 |
| Challenger Prague 2 | 2016/07/25 09:00 | Jan Mertl v Santiago Giraldo | 5-7,6-7 |
| Challenger Barranquilla | 2016/09/06 20:00 | Gregorio Cordonnier v Alejandro Falla | 4-6,1-6 |
| ATP Washington Qual | 2016/07/16 15:20 | Mackenzie McDonald v Alejandro Falla | 3-6,6-3,6-7 |
| ATP Newport Qual | 2016/07/10 16:00 | Alejandro Falla v Daniel Cox | 3-6,4-6 |
| Wimbledon Qual | 2016/06/22 12:50 | Alejandro Falla v Jozef Kovalik | 3-6,7-6,11-13 |
| Wimbledon Qual | 2016/06/21 09:30 | Alejandro Falla v Salvatore Caruso | 7-6,6-1 |
| French Open Qual | 2016/05/16 15:20 | Alejandro Falla v Carlos Berlocq | 4-6,4-6 |
| Challenger Bordeaux | 2016/05/12 15:30 | Rogerio Dutra Silva v Alejandro Falla | 6-1,6-2 |
| Challenger Bordeaux | 2016/05/10 13:30 | Alejandro Falla v Calvin Hemery | 6-2,6-0 |