Round: 46 Ground: Hardcourt outdoor
| ATP Newport | 2016/07/12 18:20 | Frank Dancevic v Ryan Harrison | 6-4,6-4 |
| Wimbledon Qual | 2016/06/21 10:50 | Bjorn Fratangelo v Ryan Harrison | 6-4,7-5 |
| French Open Qual | 2016/05/18 17:00 | Ryan Harrison v Gerald Melzer | 4-6,7-6,4-6 |
| French Open Qual | 2016/05/16 14:30 | Alessandro Giannessi v Ryan Harrison | 3-6,2-6 |
| Challenger Heilbronn | 2016/05/10 09:00 | Ryan Harrison v Renzo Olivo | 6-3,3-6,2-6 |
| Challenger Tallahassee | 2016/04/29 23:35 | Frances Tiafoe v Ryan Harrison | 7-6,6-4 |
| Challenger Tallahassee | 2016/04/28 19:30 | Noah Rubin v Ryan Harrison | 6-2,0-6,3-6 |
| Challenger Tallahassee | 2016/04/27 19:45 | Ryan Harrison v Giovanni Lapentti | 6-3,6-4 |
| ATP Washington Qual | 2016/07/16 16:40 | Ryan Shane v Amir Weintraub | 4-6,2-6 |
| ATP Newport | 2016/07/12 17:00 | Amir Weintraub v Yuichi Sugita | 6-4,3-6,2-6 |
| ATP Newport Qual | 2016/07/11 15:00 | Amir Weintraub v Frank Dancevic | 6-7,7-6,4-6 |
| ATP Newport Qual | 2016/07/10 16:00 | Amir Weintraub v Evan King | 7-6,7-6 |
| Wimbledon Qual | 2016/06/21 13:50 | Ruben Bemelmans v Amir Weintraub | 6-3,6-2 |
| French Open Qual | 2016/05/17 11:10 | Jordi Samper-Montana v Amir Weintraub | 6-2,3-6,6-2 |
| ITF Turkey F15 | 2016/04/12 07:00 | Amir Weintraub v Matteo Herrmann-Zunic | 6-3,2-6,6-2 |
| ITF Turkey F14 | 2016/04/07 10:25 | Amir Weintraub v Lukas Mugevicius | 6-7,6-0,4-6 |