Round: 46 Ground: Hardcourt outdoor
| US Open Qual | 2016/08/24 22:25 | Jared Donaldson v Eduardo Struvay | 6-3,6-4 |
| ATP Cincinnati | 2016/08/16 23:55 | Jared Donaldson v Stan Wawrinka | 6-2,3-6,4-6 |
| ATP Cincinnati | 2016/08/15 15:00 | Jared Donaldson v Nicolas Almagro | 6-3,7-6 |
| ATP Washington | 2016/07/20 00:20 | Jared Donaldson v Benoit Paire | 0-6,5-7 |
| ATP Washington | 2016/07/19 01:35 | Vincent Millot v Jared Donaldson | 7-5,2-6,4-6 |
| ATP Washington Qual | 2016/07/17 16:35 | Jared Donaldson v Marinko Matosevic | 7-6,6-4 |
| ATP Newport | 2016/07/11 19:45 | Jared Donaldson v Donald Young | 1-6,3-6 |
| French Open Qual | 2016/05/20 11:35 | Nikoloz Basilashvili v Jared Donaldson | 4-6,7-5,6-2 |
| 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 |
| Davis Cup | 2016/07/16 14:00 | Nicolas Jarry v Santiago Giraldo | 2-6,4-6,3-6 |
| Wimbledon | 2016/06/27 16:10 | Santiago Giraldo v Gilles Muller | 6-4,7-6,6-7,3-6,13-15 |