Stadium: Centre Court Round: 25 Ground: Hardcourt indoor
| ATP Metz | 2018/09/23 13:45 | Matthias Bachinger v Gilles Simon | 6-7,1-6 |
| ATP Metz | 2018/09/22 12:00 | Gilles Simon v Radu Albot | 6-3,6-1 |
| ATP Metz | 2018/09/21 14:05 | Gilles Simon v Richard Gasquet | 7-6,6-2 |
| ATP Metz | 2018/09/20 15:20 | Filip Krajinovic v Gilles Simon | 6-4,5-7,5-7 |
| ATP Metz | 2018/09/19 16:00 | Gilles Simon v Jiri Vesely | 7-5,6-3 |
| US Open | 2018/08/29 16:25 | Milos Raonic v Gilles Simon | 6-3,6-4,6-4 |
| US Open | 2018/08/27 15:00 | Lloyd Harris v Gilles Simon | 2-6,2-6,3-6 |
| ATP Kitzbuhel | 2018/07/31 15:00 | Gilles Simon v Matteo Berrettini | 6-1,3-6,4-6 |
| ATP Metz | 2018/09/16 14:00 | Sergiy Stakhovsky v Maxime Janvier | 3-6,4-6 |
| Davis Cup | 2018/09/15 10:00 | Sergiy Stakhovsky v Joao Sousa | 6-2,4-6,6-4 |
| Davis Cup | 2018/09/14 11:30 | Sergiy Stakhovsky v Pedro Sousa | 6-3,6-2 |
| Challenger Cassis | 2018/09/04 13:05 | Oscar Otte v Sergiy Stakhovsky | 7-6,3-6,7-5 |
| Challenger Mallorca | 2018/08/30 09:30 | Kenny de Schepper v Sergiy Stakhovsky | 6-2,6-4 |
| Challenger Mallorca | 2018/08/29 10:30 | Emilio Gomez v Sergiy Stakhovsky | 4-6,6-7 |
| US Open | 2018/08/22 16:30 | Thai-Son Kwiatkowski v Sergiy Stakhovsky | 6-4,3-6,6-1 |
| Challenger Portoroz | 2018/08/09 18:00 | Sergiy Stakhovsky v Constant Lestienne | 6-3,2-6,1-6 |