Round: 28 Ground: Clay
| Challenger - Savannah | 2016/04/22 16:00 | Jared Donaldson v Gerald Melzer | 6-4,6-7,6-4 |
| Challenger - Savannah | 2016/04/20 16:30 | Jared Donaldson v Guido Andreozzi | 1-6,7-5,7-6 |
| Challenger - Savannah | 2016/04/18 21:30 | Jared Donaldson v Ryan Harrison | 6-2,7-6 |
| Challenger Sarasota | 2016/04/11 18:15 | Nicolas Kicker v Jared Donaldson | 6-2,6-1 |
| ATP Houston Qual | 2016/04/03 17:30 | Jared Donaldson v Nicolas Kicker | 6-4,1-6,6-7 |
| ATP Houston Qual | 2016/04/02 18:05 | Jared Donaldson v Henri Laaksonen | 6-1,2-6,6-4 |
| ATP Miami | 2016/03/23 21:15 | Yoshihito Nishioka v Jared Donaldson | 6-3,6-4 |
| ATP Miami Qual | 2016/03/22 19:00 | Jared Donaldson v Alejandro Gonzalez | 2-6,6-3,2-6 |
| Challenger - Savannah | 2016/04/22 19:10 | Nicolas Kicker v Donald Young | 4-6,5-7 |
| Challenger - Savannah | 2016/04/18 23:25 | Noah Rubin v Donald Young | 5-7,6-7 |
| ATP Houston | 2016/04/07 18:00 | Donald Young v Tim Smyczek | 2-6,4-6 |
| ATP Houston | 2016/04/05 18:20 | Steve Johnson v Donald Young | 4-6,3-6 |
| ATP Miami | 2016/03/24 15:00 | Andreas Seppi v Donald Young | 6-3,6-1 |
| ATP Delray Beach | 2016/02/18 17:30 | Tim Smyczek v Donald Young | 1-6,7-6,6-2 |
| ATP Memphis | 2016/02/12 21:00 | Ricardas Berankis v Donald Young | 7-6,6-1 |
| ATP Memphis | 2016/02/11 21:00 | Marcel Granollers v Donald Young | 1-6,6-7 |