Round: 24 Ground: Hardcourt outdoor
| ATP Washington Qual | 2016/07/17 16:55 | Harrison, Ryan v Weintraub, Amir | 6-4,6-3 |
| 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 |
| Hamburg, Germany | 2016/07/16 15:05 | Robert, Stephane v Martin Klizan | 3-6,4-6 |
| Hamburg, Germany | 2016/07/15 10:40 | Garcia-Lopez, Guillermo v Robert, Stephane | 6-7,6-4,3-6 |
| Hamburg, Germany | 2016/07/14 09:00 | Robert, Stephane v Cervantes, Inigo | 7-5,4-6,6-1 |
| Hamburg, Germany | 2016/07/12 09:00 | Mayer, Leonardo v Robert, Stephane | 6-7,4-6 |
| Wimbledon, London, Great Britain | 2016/06/28 12:55 | Robert, Stephane v DEL POTRO J.M. | 1-6,5-7,0-6 |
| Open de France | 2016/05/26 12:45 | Robert, Stephane v Alexander Zverev | 1-6,6-3,1-6,4-6 |
| Open de France | 2016/05/24 14:30 | Anderson, Kevin v Robert, Stephane | 4-6,2-6,6-1,5-7 |
| Challenger - Aix en Provence | 2016/05/03 08:30 | Tristan Lamasine v Robert, Stephane | 7-6,3-6,6-3 |