Stadium: CENTER COURT Round: 26 Ground: Hardcourt indoor
| ATP Stuttgart | 2016/06/09 09:00 | Jan-Lennard Struff v Gilles Simon | 4-6,6-4,2-6 |
| Davis Cup | 2015/03/06 13:00 | Jan-Lennard Struff v Gilles Simon | 6-7,6-2,7-6,2-6,8-10 |
| US Open | 2016/08/30 22:20 | Gilles Simon v Radek Stepanek | 6-3,6-1,6-4 |
| ATP Cincinnati | 2016/08/16 00:10 | Gilles Simon v Grigor Dimitrov | 1-6,3-6 |
| Wimbledon | 2016/06/29 16:55 | Grigor Dimitrov v Gilles Simon | 6-3,7-6,4-6,6-4 |
| Wimbledon | 2016/06/27 11:55 | Janko Tipsarevic v Gilles Simon | 6-4,4-6,5-7,3-6 |
| ATP Stuttgart | 2016/06/10 16:00 | Juan Martin Del Potro v Gilles Simon | 6-7,6-3,6-0 |
| ATP Stuttgart | 2016/06/09 09:00 | Jan-Lennard Struff v Gilles Simon | 4-6,6-4,2-6 |
| French Open | 2016/05/27 16:15 | Gilles Simon v Viktor Troicki | 4-6,2-6,2-6 |
| French Open | 2016/05/25 12:45 | Gilles Simon v Guido Pella | 4-6,1-6,7-5,7-6,6-4 |
| US Open 2016 | 2016/08/30 20:35 | Donald Young v Jan-Lennard Struff | 6-3,7-5,4-6,7-5 |
| ATP Kitzbuhel | 2016/07/21 12:00 | Paolo Lorenzi v Jan-Lennard Struff | 6-2,6-7,7-5 |
| ATP Kitzbuhel | 2016/07/20 09:30 | Daniel Munoz-De La Nava v Jan-Lennard Struff | 5-7,5-7 |
| ATP Kitzbuhel | 2016/07/19 09:30 | Akira Santillan v Jan-Lennard Struff | 2-6,2-6 |
| ATP Hamburg | 2016/07/12 16:30 | Jan-Lennard Struff v Daniil Medvedev | 4-6,7-5,4-6 |
| Wimbledon | 2016/06/27 15:45 | Daniel Evans v Jan-Lennard Struff | 6-3,6-7,7-6,7-5 |
| ATP Halle | 2016/06/15 13:35 | Roger Federer v Jan-Lennard Struff | 6-4,7-6 |
| ATP Stuttgart | 2016/06/09 09:00 | Jan-Lennard Struff v Gilles Simon | 4-6,6-4,2-6 |