| ITF USA F36 | 11/10 16:00 | 27 | Sekou Bangoura v Oliver Crawford | 7-6,6-0 | |
| ITF USA F36 | 11/09 17:45 | 26 | Oliver Crawford v Alexios Halebian | 6-7,6-3,6-3 | |
| ITF USA F36 | 11/08 14:00 | 25 | Thales Turini v Oliver Crawford | 4-6,0-6 | |
| ITF USA F15 | 04/26 16:00 | 25 | Calvin Hemery v Oliver Crawford | 6-4,3-6,6-4 | |
| ITF USA F15 | 04/25 14:00 | 60 | Oliver Crawford v Mac Kiger | 6-2,6-1 | |
| ITF USA F15 | 04/21 13:00 | 60 | Oliver Crawford v Brant Vaughan Switzler | 6-1,6-0 | |
| ITF USA F14 | 04/16 14:00 | 60 | Pavel Krainik v Oliver Crawford | 6-4,6-4 | |
| ITF USA F14 | 04/15 15:00 | 60 | Drew Van Orderlain v Oliver Crawford | 1-6,2-6 | |
| ITF USA F5 | 01/25 15:00 | 25 | Oliver Crawford v Juan P Varillas | 2-6,3-6 | |
| ITF USA F37 | 11/16 19:25 | 25 | Maxime Chazal v Oliver Crawford | 7-5,6-2 | |
| ITF USA F37 | 11/14 16:00 | 60 | Dominic Cotrone v Oliver Crawford | 4-6,4-6 | |
| ITF USA F37 | 11/12 20:30 | 60 | Yates Johnson v Oliver Crawford | 2-6,5-7 | |
| ITF USA F37 | 11/11 23:30 | 60 | Emmett Ward v Oliver Crawford | 2-6,2-6 | |
| ITF USA F36 | 11/09 18:10 | 25 | Oliver Crawford v Lukas Ollert | 2-6,2-6 | |
| ITF USA F36 | 11/07 15:30 | 60 | Oliver Crawford v Noe Khlif | 6-3,6-1 | |
| ITF USA F8 | 02/25 16:30 | 26 | Oliver Crawford v Jonathan Eysseric | 2-6,3-6 | |
| ITF USA F8 | 02/24 16:30 | 25 | Oliver Crawford v Peter Torebko | 6-3,0-6,7-6 | |
| ITF USA F8 Qual | 02/22 17:00 | 60 | Reilly Opelka v Oliver Crawford | 3-6,4-6 | |
| ITF USA F8 Qual | 02/21 17:00 | 60 | Oliver Crawford v Oscar Gabriel Ortiz | 6-2,6-4 | |
| ITF USA F8 Qual | 02/19 17:30 | 60 | Oliver Crawford v Oscar Matias Leiva Biason | 6-2,6-0 | |
| ITF USA F7 Qual | 02/13 17:00 | 60 | Gianni Ross v Oliver Crawford | 7-5,6-7,6-4 | |
| ITF USA F7 Qual | 02/12 15:30 | 60 | Oliver Crawford v Alexandre Rotsaert | 7-6,6-3 | |
| ITF USA F6 | 02/01 14:30 | 60 | Maciej Rajski v Oliver Crawford | 6-4,6-2 | |
| ITF USA F6 | 01/30 14:00 | 60 | Oliver Crawford v Piotr Zbroja | 6-1,6-0 | |
| ITF USA F5 | 01/25 15:30 | 60 | Omar Salman v Oliver Crawford | 6-2,6-7,6-2 | |
| ITF USA F5 | 01/22 16:00 | 60 | Oliver Crawford v Farzin Danny Amiri | 6-1,6-1 | |
| ITF USA F4 | 01/18 14:30 | 60 | Oliver Crawford v Hady Habib | 3-6,6-3,6-7 | |
| ITF USA F4 | 01/17 18:00 | 60 | Ryota Tanuma v Oliver Crawford | 1-6,4-6 | |
| ITF USA F4 | 01/15 13:00 | 60 | John McNally v Oliver Crawford | 5-7,6-7 |