[38] Gilles Simon 6-1,4-6,6-4 Kevin Anderson [8] 2019-06-20 10:00
Stadium: Court 1 Round: 26 Ground: Grass
Head to Head
| ATP Pune | 2019/01/04 15:40 | Kevin Anderson v Gilles Simon | 6-3,7-6 |
| ATP Pune | 2018/01/06 11:30 | Gilles Simon v Kevin Anderson | 7-6,6-2 |
| ATP Tokyo | 2017/10/02 06:40 | Gilles Simon v Kevin Anderson | 2-6,6-7 |
Home History
| ATP Queens | 2019/06/17 16:55 | Gilles Simon v James Ward | 3-6,6-3,7-6 |
| ATP Stuttgart | 2019/06/13 15:30 | Gilles Simon v Felix Auger Aliassime | 5-7,4-6 |
| ATP Stuttgart | 2019/06/11 13:40 | Peter Gojowczyk v Gilles Simon | 6-4,2-6,3-6 |
| French Open | 2019/05/30 10:10 | Salvatore Caruso v Gilles Simon | 6-1,6-2,6-4 |
| French Open | 2019/05/27 13:15 | Sergiy Stakhovsky v Gilles Simon | 3-6,3-6,4-6 |
| ATP Rome | 2019/05/12 10:55 | Philipp Kohlschreiber v Gilles Simon | 6-2,3-6,6-3 |
| ATP Madrid | 2019/05/07 12:05 | Gilles Simon v Hugo Dellien | 6-4,1-6,6-7 |
| ATP Barcelona | 2019/04/24 10:30 | Mackenzie McDonald v Gilles Simon | 6-3,6-2 |
Away History
| ATP Queens | 2019/06/17 14:15 | Cameron Norrie v Kevin Anderson | 6-4,6-7,4-6 |
| ATP Miami | 2019/03/28 23:40 | Kevin Anderson v Roger Federer | 0-6,4-6 |
| ATP Miami | 2019/03/26 20:15 | Kevin Anderson v Jordan Thompson | 7-5,7-5 |
| ATP Miami | 2019/03/25 16:00 | Kevin Anderson v Joao Sousa | 6-4,7-6 |
| ATP Miami | 2019/03/23 17:20 | Kevin Anderson v Jaume Munar | 6-4,3-6,6-3 |
| Australian Open | 2019/01/16 02:05 | Kevin Anderson v Frances Tiafoe | 6-4,4-6,4-6,5-7 |
| Australian Open | 2019/01/14 00:00 | Kevin Anderson v Adrian Mannarino | 6-3,5-7,6-2,6-1 |
| Kooyong Classic | 2019/01/09 00:00 | Marin Cilic v Kevin Anderson | 6-3,4-6,15-13 |