Round: 25 Ground: Grass
| Challenger - Savannah | 2016/04/23 19:25 | Jared Donaldson v Donald Young | 6-4,6-3 |
| French Open - Qualifikation | 2016/05/20 11:35 | Nikoloz Basilashvili v Jared Donaldson | 4-6,7-5,6-2 |
| French Open - Qualifikation | 2016/05/19 12:40 | Axel Michon v Jared Donaldson | 3-6,6-7 |
| Challenger - Bordeaux | 2016/05/12 13:15 | Andre Ghem v Jared Donaldson | 6-3,6-4 |
| Challenger - Bordeaux | 2016/05/10 08:30 | Jared Donaldson v Thiemo De Bakker | 6-2,6-4 |
| Challenger - Tallahassee | 2016/04/26 18:00 | Jared Donaldson v Calvin Hemery | 4-6,3-6 |
| Challenger - Savannah | 2016/04/24 19:20 | Bjorn Fratangelo v Jared Donaldson | 6-1,6-3 |
| Challenger - Savannah | 2016/04/23 19:25 | Jared Donaldson v Donald Young | 6-4,6-3 |
| Challenger - Savannah | 2016/04/22 16:00 | Jared Donaldson v Gerald Melzer | 6-4,6-7,6-4 |
| Wimbledon | 2016/07/01 10:30 | Lucas Pouille v Donald Young | 6-4,6-3,6-3 |
| Wimbledon | 2016/06/28 14:40 | Donald Young v Leonardo Mayer | 6-4,7-5,3-6,6-3 |
| French Open | 2016/05/22 09:00 | Teymuraz Gabashvili v Donald Young | 7-6,6-2,6-3 |
| Challenger - Tallahassee | 2016/04/28 23:55 | Donald Young v Frances Tiafoe | 6-2,4-6,3-6 |
| Challenger - Tallahassee | 2016/04/27 16:25 | Donald Young v Daniil Medvedev | 6-4,7-6 |
| Challenger - Tallahassee | 2016/04/26 21:20 | Donald Young v Ernesto Escobedo | 6-3,6-4 |
| Challenger - Savannah | 2016/04/23 19:25 | Jared Donaldson v Donald Young | 6-4,6-3 |
| Challenger - Savannah | 2016/04/22 19:10 | Nicolas Kicker v Donald Young | 4-6,5-7 |