| ITF M25 Gandia | 07/21 16:00 | 27 | Oliver Crawford v Diego A B Sanchez | 3-6,7-6,6-1 | |
| ITF M25 Gandia | 07/20 15:55 | 26 | Oliver Crawford v Nil Regas Luis | 6-2,6-2 | |
| ITF M25 Gandia | 07/19 17:30 | 25 | Oliver Crawford v Max Alcala Gurri | 6-3,1-6,6-1 | |
| ITF M25 Padova | 07/14 13:00 | 27 | [274] Oliver Crawford v Samuel Vincent Ruggeri [423] | 5-7,4-6 | |
| ITF M25 Padova | 07/13 16:10 | 26 | Oliver Crawford v Alessandro Pecci | 6-3,6-7,6-4 | |
| ITF M25 Padova | 07/12 13:00 | 25 | Oliver Crawford v Giuseppe Tresca | 6-4,6-2 | |
| ITF M25 Klosters | 07/09 08:00 | 29 | [274] Oliver Crawford v Damien Wenger [419] | 6-1,6-3 | |
| ITF M25 Klosters | 07/08 11:10 | 28 | [274] Oliver Crawford v Benjamin Lock [330] | 3-6,6-4,6-0 | |
| ITF M25 Klosters | 07/07 08:00 | 27 | [274] Oliver Crawford v Mili Poljicak [466] | 1-6,6-3,6-3 | |
| ITF M25 Klosters | 07/06 10:05 | 26 | Oliver Crawford v Pierre Delage | 6-3,6-3 | |
| ITF M25 Klosters | 07/05 07:00 | 25 | Oliver Crawford v Henry V-D Schulenburg | 6-4,6-3 | |
| Challenger Modena | 06/27 13:45 | 25 | [273] Oliver Crawford v Moez Echargui [310] | 4-6,5-7 | |
| ITF M25 Mungia | 06/22 15:25 | 27 | [271] Oliver Crawford v Henrique Rocha [348] | 1-6,7-6,2-6 | |
| ITF M25 Mungia | 06/21 16:10 | 26 | Oliver Crawford v Matyas Fuele | 6-4,6-3 | |
| ITF M25 Mungia | 06/20 11:25 | 25 | [271] Oliver Crawford v Imanol L Morillo [434] | 6-3,6-4 | |
| ITF M25 Rome | 06/01 09:00 | 27 | [264] Oliver Crawford v Alex Barrena [500] | 6-0,2-6,1-6 | |
| ITF M25 Rome | 05/31 10:05 | 26 | [264] Oliver Crawford v Marcello Serafini [499] | 7-5,7-5 | |
| ITF M25 Rome | 05/30 13:35 | 25 | Oliver Crawford v Giammarco Gandolfi | 6-0,6-3 | |
| Challenger Skopje | 05/25 09:30 | 27 | [273] Francisco Comesana v Oliver Crawford [281] | 6-4,6-1 | |
| Challenger Skopje | 05/24 09:00 | 26 | [287] Max Houkes v Oliver Crawford [281] | 4-6,2-6 | |
| Challenger Skopje | 05/23 08:30 | 25 | [281] Oliver Crawford v Matheus P De Almeida [247] | 6-3,7-6 | |
| ITF M25 Kursumlijska Banja | 05/19 10:05 | 27 | [483] Marko Topo v Oliver Crawford [295] | 6-3,6-1 | |
| ITF M25 Kursumlijska Banja | 05/18 14:00 | 26 | Mwendwa Mbithi v Oliver Crawford | 0-6,2-6 | |
| ITF M25 Kursumlijska Banja | 05/17 11:15 | 25 | Johan A R Rodriguez v Oliver Crawford | 3-6,4-6 | |
| ITF M25 Varnamo | 05/14 08:15 | 29 | Dragos Nicolae Madaras v Oliver Crawford | 7-6,6-1 | |
| ITF M25 Varnamo | 05/13 08:15 | 28 | [336] Jay Clarke v Oliver Crawford [295] | 7-5,6-7,6-7 | |
| ITF M25 Varnamo | 05/12 10:00 | 27 | Elmer Moeller v Oliver Crawford | 0-6,2-6 | |
| ITF M25 Varnamo | 05/11 08:15 | 26 | Erik Grevelius v Oliver Crawford | 1-6,2-6 | |
| ITF M25 Varnamo | 05/10 09:20 | 25 | Olle Noltorp v Oliver Crawford | 1-6,0-6 | |
| Challenger Savannah | 04/24 18:00 | 25 | [290] Oliver Crawford v Facundo D Acosta [160] | 1-6,2-6 |