Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| Australian Open | 2024/01/12 00:40 | Oliver Crawford v Vít Kopřiva | 4-6,4-6 |
| Australian Open | 2024/01/11 02:55 | Francesco Passaro v Oliver Crawford | 4-6,7-6,4-6 |
| Australian Open | 2024/01/09 23:00 | Oliver Crawford v Ilya Ivashka | 6-3,3-6,6-1 |
| Challenger Brazílie | 2023/11/21 19:45 | Bernard Tomic v Oliver Crawford | 6-3,6-2 |
| Challenger Lima | 2023/11/07 18:05 | Oliver Crawford v Arklon H D Pino | 5-7,0-6 |
| Challenger Guayaquil | 2023/10/31 19:00 | Franco Agamenone v Oliver Crawford | 6-3,4-6,6-1 |
| Challenger Curitiba | 2023/10/29 18:00 | Hugo Dellien v Oliver Crawford | 7-6,4-6,7-6 |
| Challenger Curitiba | 2023/10/29 13:00 | Luciano Darderi v Oliver Crawford | 2-6,3-6 |
| ITF M25 Mandya | 2024/01/13 04:30 | Karan Singh v Jelle Sels | 1-6,4-6 |
| ITF M25 Mandya | 2024/01/12 04:30 | Kris Van Wyk v Karan Singh | 3-6,3-6 |
| ITF M25 Mandya | 2024/01/11 08:00 | Ishaque Eqbal v Karan Singh | 6-3,4-6,2-6 |
| ITF M25 Mandya | 2024/01/10 09:15 | Karan Singh v Tsung-Hao Huang | 3-6,6-3,6-2 |
| ITF M25 Kalaburagi | 2023/11/30 04:00 | Ryotaro Taguchi v Karan Singh | 7-5,6-1 |
| ITF M25 Kalaburagi | 2023/11/28 04:00 | Ranjeet Virali-Murugesan v Karan Singh | 4-6,2-6 |
| ITF M25 Mumbai | 2023/11/22 05:30 | Harrison Adams v Karan Singh | 6-4,3-6,6-1 |
| ITF M15 Davangere | 2023/10/27 04:30 | Karan Singh v Bogdan Bobrov | 5-7,0-6 |