| ITF M25 Sierre | 09/04 10:20 | 28 | Patrick Kypson v Oliver Crawford | 3-6,4-6 | |
| ITF M25 Sierre | 09/03 10:00 | 27 | Valentin Vacherot v Oliver Crawford | 3-6,6-7 | |
| ITF M25 Sierre | 09/02 12:45 | 26 | Mirko Martinez v Oliver Crawford | 1-6,2-6 | |
| ITF M25 Sierre | 09/01 13:40 | 25 | Louroi Martinez v Oliver Crawford | 3-6,4-6 | |
| ITF M25 Trier | 08/25 15:00 | 25 | Henri Squire v Oliver Crawford | 3-6,6-1,6-2 | |
| ITF M25 Ueberlingen | 08/20 10:00 | 27 | [369] Ergi Kirkin v Oliver Crawford [434] | 6-4,3-6,6-2 | |
| ITF M25 Ueberlingen | 08/19 11:45 | 26 | Aliaksandr Bulitski v Oliver Crawford | 1-6,1-6 | |
| ITF M25 Ueberlingen | 08/18 12:50 | 25 | Andres Gabriel Ciurletti v Oliver Crawford | Retired | |
| Challenger Lexington | 07/26 18:00 | 19 | [346] Darian King v Oliver Crawford [420] | 6-4,6-1 | |
| Challenger Lexington | 07/25 15:00 | 14 | [416] Oliver Crawford v Aleksandar Kovacevic [413] | 7-6,7-5 | |
| Challenger Cary | 07/18 15:00 | 14 | Oliver Crawford v Trent Bryde | 6-7,2-6 | |
| ITF M25 Tulsa | 06/17 16:00 | 26 | Oliver Crawford v Michail Pervolarakis | Walkover | |
| ITF M25 Tulsa | 06/17 00:35 | 25 | Oliver Crawford v Ryan Shane | 7-5,7-6 | |
| Challenger Orlando | 06/08 17:00 | 25 | [453] Oliver Crawford v Emilio Gomez [179] | 6-7,7-6,3-6 | |
| Challenger Little Rock | 06/04 16:00 | 27 | [317] Goncalo Oliveira v Oliver Crawford [453] | Retired | |
| Challenger Little Rock | 06/03 17:00 | 26 | [381] Dayne Kelly v Oliver Crawford [453] | 4-6,1-6 | |
| Challenger Little Rock | 06/02 16:30 | 25 | [453] Oliver Crawford v Peter Polansky [244] | 7-5,6-2 | |
| ITF M25 Pensacola | 05/21 14:25 | 27 | [364] Adrian Andreev v Oliver Crawford [457] | 6-2,6-3 | |
| ITF M25 Pensacola | 05/20 16:25 | 26 | [457] Oliver Crawford v Christian Harrison [299] | 6-4,7-6 | |
| ITF M25 Pensacola | 05/19 14:30 | 25 | Mwendwa Mbithi v Oliver Crawford | 5-7,4-6 | |
| ITF M15 Cairo | 05/08 11:05 | 28 | Simon A Ivanov v Oliver Crawford | 7-5,6-4 | |
| ITF M15 Cairo | 05/07 10:15 | 27 | Gabriel Donev v Oliver Crawford | 6-3,2-6,2-6 | |
| ITF M15 Cairo | 05/06 09:35 | 26 | Thiago Cigarran v Oliver Crawford | 1-6,5-7 | |
| ITF M15 Cairo | 05/05 12:45 | 25 | Alex Barrena v Oliver Crawford | 0-6,2-6 | |
| ITF M15 Cairo | 04/30 09:10 | 27 | Oliver Crawford v Bastian Malla | 1-6,0-6 | |
| ITF M15 Cairo | 04/29 08:00 | 26 | Oliver Crawford v Juan Ignacio Galarza | 6-1,6-4 | |
| ITF M15 Cairo | 04/28 10:20 | 25 | Oliver Crawford v Yanais Laurent | 6-2,6-2 | |
| ITF M15 Cairo | 04/25 09:00 | 29 | Oliver Crawford v Daniel Michalski | 6-2,5-7,6-3 | |
| ITF M15 Cairo | 04/24 09:00 | 28 | Benjamin Winter Lopez v Oliver Crawford | 2-6,4-6 | |
| ITF M15 Cairo | 04/23 09:00 | 27 | Oliver Crawford v Jose Fco. Vidal Azorin | 6-4,2-6,7-5 |