stadio: Stadium Round: 27 Ground: Hardcourt outdoor
| Challenger Winnipeg | 2023/08/16 18:50 | Jack Draper v Thai-Son Kwiatkowski | 6-4,7-6 |
| Challenger Winnipeg | 2023/08/15 23:00 | Jack Draper v Rio Noguchi | 6-2,6-2 |
| ATP Lione | 2023/05/25 09:00 | Jack Draper v Francisco Cerundolo | 6-4,4-6,3-6 |
| ATP Lione | 2023/05/23 13:00 | Miomir Kecmanovic v Jack Draper | 4-6,5-7 |
| ATP Lione | 2023/05/21 15:45 | Jack Draper v Alexandre Muller | 6-2,6-3 |
| ATP Monte Carlo | 2023/04/11 14:55 | Hubert Hurkacz v Jack Draper | 6-3,6-7,7-5 |
| ATP Monte Carlo | 2023/04/10 10:30 | Sebastian Baez v Jack Draper | 3-6,5-7 |
| ATP Indian Wells | 2023/03/14 01:05 | Jack Draper v Andy Murray | 7-6,6-2 |
| Challenger Winnipeg | 2023/08/16 20:45 | Ulises Blanch v Arthur Cazaux | 3-6,5-7 |
| Challenger Winnipeg | 2023/08/15 18:45 | Kiranpal Pannu v Arthur Cazaux | 3-6,1-6 |
| Challenger Cary | 2023/08/10 19:30 | Arthur Cazaux v Lloyd Harris | 4-6,6-7 |
| Challenger Cary | 2023/08/09 00:35 | Arthur Cazaux v Abedallah Shelbayh | 6-3,6-0 |
| Challenger Lexington | 2023/08/06 17:00 | Arthur Cazaux v Steve Johnson | 6-7,4-6 |
| Challenger Lexington | 2023/08/05 20:00 | Arthur Cazaux v Cannon Kingsley | 6-2,7-6 |
| Challenger Lexington | 2023/08/04 19:00 | Arthur Cazaux v Aidan Mayo | 6-1,6-4 |
| Challenger Lexington | 2023/08/04 01:10 | Arthur Cazaux v Omar Jasika | 6-2,6-3 |