Stadium: Show Court 1 Round: 14 Ground: Hardcourt outdoor
| Davis Cup | 2023/11/23 17:10 | Miomir Kecmanovic v Jack Draper | 7-6,7-6 |
| ATP Sofia | 2023/11/11 13:00 | Jack Draper v Adrian Mannarino | 6-7,6-2,3-6 |
| ATP Sofia | 2023/11/10 14:00 | Jack Draper v Jan-Lennard Struff | 6-3,6-4 |
| ATP Sofia | 2023/11/09 13:15 | Jack Draper v Cem Ilkel | 6-2,6-2 |
| 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 |
| ATP Brisbane | 2023/12/30 03:20 | Dominic Thiem v James McCabe | 2-6,7-6,6-4 |
| Challenger Kobe | 2023/11/14 04:55 | Benjamin Hassan v James McCabe | 0-6,6-3,6-2 |
| Challenger Matsuyama | 2023/11/08 01:00 | James McCabe v Luca Nardi | 4-6,4-6 |
| Challenger Matsuyama | 2023/11/06 02:30 | Frederico Ferreira Silva v James McCabe | 3-6,2-6 |
| ATP Shanghai | 2023/10/03 04:30 | James Duckworth v James McCabe | 7-6,6-2 |
| ATP Shanghai | 2023/10/02 06:15 | Linang Xiao v James McCabe | 4-6,7-6,3-6 |
| Challenger Zhangjiagang | 2023/09/01 05:35 | Rigele Te v James McCabe | 6-7,6-3,0-6 |
| Challenger Zhangjiagang | 2023/08/31 06:20 | Lorenzo Giustino v James McCabe | 4-6,6-3,1-6 |