Stadium: Center Court Round: 27 Ground: Hardcourt indoor
| ATP Sofia | 2023/11/08 17:05 | Lorenzo Musetti v Jack Draper | 5-7,2-6 |
| ATP Sofia | 2023/11/07 20:35 | Jack Draper v Maximilian Marterer | 6-3,6-2 |
| Challenger Bergamo | 2023/11/05 15:35 | Jack Draper v David Goffin | 1-6,7-6,6-3 |
| Challenger Bergamo | 2023/11/04 15:30 | Jack Draper v Brandon Nakashima | 6-1,3-6,7-5 |
| Challenger Bergamo | 2023/11/03 18:00 | Jack Draper v Billy Harris | 6-2,6-3 |
| Challenger Bergamo | 2023/11/02 17:50 | Jack Draper v Andrea Vavassori | 6-3,6-4 |
| Challenger Bergamo | 2023/10/31 19:00 | Jack Draper v Francesco Maestrelli | 6-4,6-4 |
| ATP Tokio | 2023/10/17 02:00 | Alex De Minaur v Jack Draper | 4-6,7-6,7-6 |
| ATP Sofia | 2023/11/08 14:40 | Cem Ilkel v Max Purcell | 6-3,4-6,6-4 |
| ATP Sofia | 2023/11/07 18:15 | Cem Ilkel v Dimitar Kuzmanov | 6-0,6-3 |
| Challenger Bergamo | 2023/11/02 16:15 | Cem Ilkel v Pierre-Hugues Herbert | 1-6,1-6 |
| Challenger Bergamo | 2023/10/31 18:30 | Cem Ilkel v Illya Marchenko | 6-7,6-4,7-5 |
| Challenger Hamburg | 2023/10/19 15:05 | Cem Ilkel v Billy Harris | 6-7,1-6 |
| Challenger Bratysława | 2023/10/10 09:08 | Cem Ilkel v Jakub Mensik | 0-0 |
| Challenger Bratysława | 2023/10/09 08:30 | Cem Ilkel v Gabi Adrian Boitan | 2-6,1-6 |
| Challenger Bratysława | 2023/10/08 09:00 | Cem Ilkel v Maxim Mrva | 6-1,6-4 |