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