Round: 23 Ground: Hardcourt outdoor
| 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 |
| French Open | 2016/05/23 14:15 | Gilles Simon v Rogerio Dutra Silva | 7-6,6-4,6-2 |
| Wimbledon | 2016/06/28 10:30 | Nick Kyrgios v Radek Stepanek | 6-4,6-3,6-7,6-1 |
| ATP Stuttgart | 2016/06/10 14:00 | Philipp Kohlschreiber v Radek Stepanek | 6-4,7-5 |
| ATP Stuttgart | 2016/06/09 12:25 | Radek Stepanek v Marin Cilic | 7-6,7-5 |
| ATP Stuttgart | 2016/06/07 09:00 | Denis Istomin v Radek Stepanek | 5-7,6-3,3-6 |
| ATP Stuttgart Qual | 2016/06/05 11:40 | Radek Stepanek v James Ward | 6-2,6-1 |
| ATP Stuttgart Qual | 2016/06/04 15:20 | Radek Stepanek v Nikola Mektic | 6-4,6-3 |
| French Open | 2016/05/23 17:00 | Radek Stepanek v Andy Murray | 6-3,6-3,0-6,3-6,5-7 |
| French Open Qual | 2016/05/20 08:00 | Yoshihito Nishioka v Radek Stepanek | 3-6,2-6 |