| Challenger - Savannah | 2016/04/20 00:00 | Tim Smyczek v Frances Tiafoe | 4-6,2-6 |
| Challenger Sarasota | 2016/04/12 21:00 | Frances Tiafoe v Tim Smyczek | 6-4,6-3 |
| ATP Houston | 2016/04/08 18:35 | Tim Smyczek v Feliciano Lopez | 2-6,3-6 |
| ATP Houston | 2016/04/07 18:00 | Donald Young v Tim Smyczek | 2-6,4-6 |
| 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 |
| Challenger - Savannah | 2016/04/21 16:30 | Denis Kudla v Brian Baker | 6-3,6-3 |
| Challenger - Savannah | 2016/04/18 20:15 | Brian Baker v Tommy Paul | 6-3,6-1 |
| ATP Houston Qual | 2016/04/03 16:00 | Carlos Berlocq v Brian Baker | 6-4,6-0 |
| ATP Houston Qual | 2016/04/02 16:30 | Brian Baker v Guilherme Clezar | 6-2,7-6 |
| ATP Miami | 2016/03/24 18:15 | Brian Baker v Mikhail Kukushkin | 4-6,2-6 |