Stadium: Central Arena Round: 26 Ground: Hardcourt indoor
| Challenger - Orleans | 2023/09/27 10:00 | Jack Draper v Radu Albot | 6-2,6-2 |
| Davis Cup | 2023/09/13 12:00 | Thanasi Kokkinakis v Jack Draper | 7-6,3-6,6-7 |
| US Open | 2023/09/04 17:40 | Jack Draper v Andrey Rublev | 3-6,6-3,3-6,4-6 |
| US Open | 2023/09/02 15:00 | Michael Mmoh v Jack Draper | 4-6,2-6,6-3,3-6 |
| US Open | 2023/08/31 15:00 | Jack Draper v Hubert Hurkacz | 6-2,6-4,7-5 |
| US Open | 2023/08/29 20:00 | Radu Albot v Jack Draper | 1-6,4-6,3-6 |
| ATP - Winston-Salem | 2023/08/21 18:00 | Nuno Borges v Jack Draper | 3-6,1-6 |
| Challenger - Winnipeg | 2023/08/17 23:00 | Jack Draper v Arthur Cazaux | 3-6,3-6 |
| Challenger - Orleans | 2023/09/26 20:10 | Tristan Lamasine v Remy Bertola | 2-6,6-3,7-5 |
| Challenger - Orleans | 2023/09/25 08:30 | Tristan Lamasine v Norbert Gombos | 7-6,6-2 |
| Challenger - Orleans | 2023/09/24 10:25 | Gabriel Debru v Tristan Lamasine | 4-6,6-7 |
| ITF - M25 Plaisir | 2023/09/16 13:55 | Antoine Hoang v Tristan Lamasine | 6-4,6-2 |
| ITF - M25 Plaisir | 2023/09/15 10:55 | Tristan Lamasine v Daniel Little | 6-1,6-4 |
| ITF - M25 Plaisir | 2023/09/14 15:30 | Tristan Lamasine v Daniil Glinka | 4-6,6-2,6-1 |
| ITF - M25 Plaisir | 2023/09/13 11:40 | Tristan Lamasine v Liova Ajavon | 6-1,6-4 |
| ITF - M25 Bagneres-De-Bigorre | 2023/09/10 13:55 | Michael Geerts v Tristan Lamasine | 6-3,3-6,7-6 |