| ATP Montpellier | 02/23 13:45 | 25 | [102] Dennis Novak v Gilles Simon [68] | 7-6,1-6,6-3 | |
| Australian Open | 02/09 09:10 | 23 | [6] Stefanos Tsitsipas v Gilles Simon [66] | 6-1,6-2,6-1 | |
| ATP Murray River Open | 02/03 05:20 | 25 | [66] Jeremy Chardy v Gilles Simon [64] | 6-3,6-4 | |
| ATP Murray River Open | 02/02 07:10 | 24 | [204] Elias Ymer v Gilles Simon [64] | 4-6,4-6 | |
| ATP Sofia | 11/11 10:00 | 26 | [38] John Millman v Gilles Simon [62] | 7-5,6-7,6-2 | |
| ATP Sofia | 11/10 10:00 | 25 | [62] Gilles Simon v Andrej Martin [105] | 6-2,6-2 | |
| ATP Sofia | 11/08 11:00 | 164 | [59] Gilles Simon v Illya Marchenko [216] | 6-2,6-3 | |
| ATP Sofia | 11/07 12:10 | 64 | [59] Gilles Simon v Luke Saville [365] | 6-4,6-3 | |
| ATP Sofia | 11/07 11:30 | 64 | Gilles Simon v Matija Pecotic | Cancelled | |
| ATP Parigi | 11/03 13:50 | 24 | [59] Gilles Simon v Tommy Paul [55] | 6-3,3-6,3-6 | |
| ATP Colonia 2 | 10/23 12:00 | 27 | [58] Gilles Simon v Jannik Sinner [46] | 3-6,6-0,4-6 | |
| ATP Colonia 2 | 10/22 13:35 | 26 | [12] Denis Shapovalov v Gilles Simon [58] | 1-6,6-4,2-6 |