Round: 24 Ground: Hardcourt outdoor
| ATP Washington Qual | 2016/07/17 16:55 | Ryan Harrison v Amir Weintraub | 6-4,6-3 |
| 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 |
| ATP Hamburg | 2016/07/16 15:05 | Stephane Robert v Martin Klizan | 3-6,4-6 |
| ATP Hamburg | 2016/07/15 10:40 | Guillermo Garcia-Lopez v Stephane Robert | 6-7,6-4,3-6 |
| ATP Hamburg | 2016/07/14 09:00 | Stephane Robert v Inigo C Huegun | 7-5,4-6,6-1 |
| ATP Hamburg | 2016/07/12 09:00 | Leonardo Mayer v Stephane Robert | 6-7,4-6 |
| Wimbledon | 2016/06/28 12:55 | Stephane Robert v Juan Martin Del Potro | 1-6,5-7,0-6 |
| French Open | 2016/05/26 12:45 | Stephane Robert v Alexander Zverev | 1-6,6-3,1-6,4-6 |
| French Open | 2016/05/24 14:30 | Kevin Anderson v Stephane Robert | 4-6,2-6,6-1,5-7 |
| Challenger Aix en Provence | 2016/05/03 08:30 | Tristan Lamasine v Stephane Robert | 7-6,3-6,6-3 |