Stadium: Court 8 Round: 14 Ground: Hardcourt outdoor
| Challenger Rennes | 2021/09/14 18:55 | Gilles Simon v Teymuraz Gabashvili | 3-6,2-6 |
| ATP Winston-Salem | 2021/08/24 19:00 | Benoit Paire v Gilles Simon | 6-3,6-3 |
| ATP Winston-Salem | 2021/08/23 01:10 | Arthur Rinderknech v Gilles Simon | 5-7,3-6 |
| Challenger San Marino | 2021/08/12 19:45 | Maxime Janvier v Gilles Simon | 7-5,6-1 |
| Challenger San Marino | 2021/08/10 18:15 | Marco De Rossi v Gilles Simon | 3-6,3-6 |
| Challenger Cordenons | 2021/08/02 18:35 | Gian Marco Moroni v Gilles Simon | 7-6,6-4 |
| Olympics 2020 - Men | 2021/07/24 05:45 | Egor Gerasimov v Gilles Simon | 4-6,6-3,6-4 |
| Wimbledon | 2021/06/29 10:00 | Dusan Lajovic v Gilles Simon | 6-4,7-5,3-6,4-6,6-3 |
| UTR Pro Tennis Series Brisbane | 2021/07/29 00:30 | Edward Winter v Jeremy Jin | 2-6,6-2,6-0 |
| UTR Pro Tennis Series Brisbane | 2021/07/27 23:00 | Edward Winter v Alexander Crnokrak | 6-1,2-6,3-6 |
| UTR Pro Tennis Series Brisbane | 2021/07/26 23:00 | Edward Winter v Tom Evans | 6-1,5-4 |
| UTR Pro Tennis Series Brisbane | 2021/07/26 00:00 | Edward Winter v Pavle Marinkov | 6-2,1-6,6-2 |
| UTR Pro Tennis Series Adelaide | 2021/06/05 04:00 | Edward Winter v Tomislav E Papac | 6-0,6-4 |
| UTR Pro Tennis Series Adelaide | 2021/06/04 07:00 | Edward Winter v Blake Bayldon | 6-0,7-6 |
| UTR Pro Tennis Series Adelaide | 2021/06/03 01:00 | Edward Winter v Ken Cavrak | 6-3,3-6,4-6 |
| UTR Pro Tennis Series Adelaide | 2021/06/02 00:30 | Scott Jones v Edward Winter | 6-2,6-4 |