| ATP Delray Beach | 2016/02/18 17:30 | Tim Smyczek v Donald Young | 1-6,7-6,6-2 |
| 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 |
| Challenger Shanghai | 2015/10/12 07:15 | Victor Estrella Burgos v Donald Young | 6-2,4-6,6-4 |
| Challenger Shanghai | 2015/10/11 04:00 | Donald Young v Andrey Kuznetsov | 3-6,1-6 |
| Challenger Shanghai | 2015/10/10 04:00 | Donald Young v Zhuoyang Qiu | 6-4,6-0 |
| ATP Houston | 2016/04/05 18:00 | Nicolas Kicker v Tim Smyczek | 6-4,6-7,4-6 |
| ATP Miami | 2016/03/28 22:00 | Tim Smyczek v Nick Kyrgios | 4-6,4-6 |
| ATP Miami | 2016/03/26 21:40 | John Isner v Tim Smyczek | 2-6,6-2,6-7 |
| ATP Miami | 2016/03/24 16:35 | Tommy Paul v Tim Smyczek | 4-6,7-5,5-7 |
| ATP Miami Qual | 2016/03/22 14:00 | Tim Smyczek v Grega Zemlja | 6-2,6-3 |
| ATP Miami Qual | 2016/03/21 15:50 | Tim Smyczek v Christian Harrison | 6-4,6-2 |
| ATP Delray Beach | 2016/02/19 23:00 | Sam Querrey v Tim Smyczek | 6-7,7-6,6-4 |
| ATP Delray Beach | 2016/02/18 17:30 | Tim Smyczek v Donald Young | 1-6,7-6,6-2 |