Round: 25 Ground: Clay
| 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 |
| ATP Miami Qual | 2016/03/21 22:20 | Malek Jaziri v Jared Donaldson | 2-6,7-6,6-7 |
| ATP Delray Beach Qual | 2016/02/13 19:10 | Jared Donaldson v Dennis Novikov | 3-6,7-6,3-6 |
| ATP Memphis | 2016/02/08 21:20 | Yoshihito Nishioka v Jared Donaldson | 6-3,6-4 |
| Challenger Sarasota | 2016/04/11 19:35 | Guilherme Clezar v Ryan Harrison | 7-5,6-2 |
| ATP Miami Qual | 2016/03/21 18:50 | Horacio Zeballos v Ryan Harrison | 6-7,6-3,6-4 |
| ATP Memphis | 2016/02/11 01:30 | Kei Nishikori v Ryan Harrison | 6-2,7-5 |
| ATP Memphis | 2016/02/09 01:30 | Ryan Harrison v Frances Tiafoe | 6-7,7-6,6-4 |
| Challenger Dallas | 2016/02/03 18:30 | Ryan Harrison v Tim Smyczek | 0-6,7-5,4-6 |
| Challenger Knoxville | 2015/11/10 19:10 | Ryan Harrison v Blaz Kavcic | 2-6,4-6 |
| Challenger Charlottesville | 2015/11/05 00:05 | Henri Laaksonen v Ryan Harrison | 7-5,7-5 |
| Challenger Charlottesville | 2015/11/02 23:30 | Tennys Sandgren v Ryan Harrison | 5-7,3-6 |