| Challenger Morelos | 04/19 22:00 | 26 | [113] James Duckworth v Oliver Crawford [298] | 3-6,7-6,6-2 | |
| Challenger Morelos | 04/18 00:50 | 25 | [228] Nicolas Mejia v Oliver Crawford [298] | 6-7,6-3,3-6 | |
| Challenger Leon | 04/12 18:00 | 26 | [304] Oliver Crawford v Nicolas Mejia [234] | 6-7,6-7 | |
| Challenger Leon | 04/10 22:40 | 25 | [304] Oliver Crawford v Joao Lucas Reis da Silva [291] | 6-3,3-6,6-3 | |
| ITF M25 Mysuru | 04/01 04:00 | 28 | [312] Blake Ellis v Oliver Crawford [290] | 7-5,6-3 | |
| ITF M25 Mysuru | 03/31 06:45 | 27 | Florent Bax v Oliver Crawford | 4-6,0-6 | |
| ITF M25 Mysuru | 03/30 04:15 | 26 | Ishaque Eqbal v Oliver Crawford | 3-6,3-6 | |
| ITF M25 Mysuru | 03/29 04:00 | 25 | Manish Ganesh v Oliver Crawford | 1-6,3-6 | |
| ITF M25 Lucknow | 03/24 04:30 | 27 | [401] Sasikumar Mukund v Oliver Crawford [290] | 7-6,6-2 | |
| ITF M25 Lucknow | 03/23 06:10 | 26 | Sidharth Rawat v Oliver Crawford | 1-6,2-6 | |
| ITF M25 Lucknow | 03/22 05:50 | 25 | George Loffhagen v Oliver Crawford | 6-2,3-6,3-6 | |
| Challenger Waco | 02/27 17:00 | 19 | [324] Ulises Blanch v Oliver Crawford [287] | 7-6,6-3 | |
| Challenger Waco | 02/26 21:05 | 14 | [363] Gabriel Decamps v Oliver Crawford [317] | 4-6,3-6 | |
| ITF M25 Monastir | 02/19 11:10 | 29 | [321] Oliver Crawford v Moez Echargui [385] | 2-6,6-4,6-1 | |
| ITF M25 Monastir | 02/18 09:30 | 28 | [442] Robin Bertrand v Oliver Crawford [321] | 1-6,6-1,2-6 | |
| ITF M25 Monastir | 02/17 11:30 | 27 | [321] Oliver Crawford v Aziz Ouakaa [428] | 6-4,6-3 | |
| ITF M25 Monastir | 02/16 08:30 | 26 | Oliver Crawford v Luca Potenza | 6-3,6-4 | |
| ITF M25 Monastir | 02/15 08:30 | 25 | [321] Oliver Crawford v Andrea Picchione [379] | 6-2,6-3 | |
| ITF M25 Bath | 02/10 13:00 | 27 | Jules Marie v Oliver Crawford | 3-6,6-3,6-4 | |
| ITF M25 Bath | 02/09 11:55 | 26 | Aziz Kijametovic v Oliver Crawford | 6-4,4-6,1-6 | |
| ITF M25 Bath | 02/08 10:00 | 25 | Damian Rodriguez v Oliver Crawford | 7-6,4-6,4-6 | |
| ITF M25 Al Zahra | 01/25 11:45 | 25 | [325] Oliver Crawford v Yanki Erel [500] | 3-6,2-6 | |
| ITF M25 Doha | 01/17 12:00 | 25 | Oliver Crawford v Niels Visker | 6-4,4-6,3-6 | |
| ITF M25 Mumbai | 11/19 05:00 | 28 | [355] Oliver Crawford v Dominik Palan [466] | 6-7,1-6 | |
| ITF M25 Mumbai | 11/18 04:30 | 27 | [355] Oliver Crawford v Niki Kaliyanda Poonacha [428] | 6-2,6-0 | |
| ITF M25 Mumbai | 11/17 04:30 | 26 | Oliver Crawford v Sandesh Dattatray Kurale | 6-0,6-0 | |
| ITF M25 Mumbai | 11/16 04:00 | 25 | Oliver Crawford v Aryan Shah | 6-0,6-3 | |
| ITF M25 Indore | 11/13 05:00 | 29 | [369] Oliver Crawford v Dominik Palan [465] | 6-1,1-6,6-3 | |
| ITF M25 Indore | 11/12 05:00 | 28 | Oliver Crawford v Woobin Shin | Retired | |
| ITF M25 Indore | 11/11 05:00 | 27 | Oliver Crawford v Kazuki Nishiwaki | 6-3,2-6,6-1 |