| Challenger Savannah | 04/22 20:50 | 25 | [248] Ethan Quinn v Oliver Crawford [197] | 6-2,6-4 | |
| Challenger Tallahassee | 04/19 16:00 | 27 | Oliver Crawford v Stefan Kozlov | 2-6,2-6 | |
| Challenger Tallahassee | 04/17 17:05 | 26 | [293] Hady Habib v Oliver Crawford [202] | 3-6,4-6 | |
| Challenger Tallahassee | 04/16 15:00 | 25 | [202] Oliver Crawford v Dmitry Popko [233] | 6-0,7-6 | |
| Challenger Sarasota | 04/08 23:15 | 25 | [109] Zizou Bergs v Oliver Crawford [198] | 6-2,6-2 | |
| Challenger Città del Messico | 04/05 21:45 | 27 | [108] Thiago Agustin Tirante v Oliver Crawford [203] | 6-4,6-4 | |
| Challenger Città del Messico | 04/04 18:00 | 26 | [226] Murkel Dellien v Oliver Crawford [203] | 2-6,4-6 | |
| Challenger Città del Messico | 04/03 00:55 | 25 | [472] Ernesto Escobedo v Oliver Crawford [203] | 6-7,4-6 | |
| Challenger San Luis Potosi | 03/27 19:55 | 26 | [444] Nicolas Mejia v Oliver Crawford [203] | 6-3,6-0 | |
| Challenger San Luis Potosi | 03/26 01:15 | 25 | [377] Dominik Palan v Oliver Crawford [203] | 4-6,3-6 | |
| Challenger Merida | 03/20 00:00 | 25 | Oliver Crawford v Jacob Brumm | 6-7,6-2,3-6 | |
| Challenger Nuova Delhi | 02/27 09:20 | 25 | [190] Oliver Crawford v Evgeny Donskoy [270] | 2-6,6-2,2-6 | |
| Challenger Pune | 02/20 07:00 | 25 | Oliver Crawford v Alexey Zakharov | 6-7,3-6 | |
| ITF M25 Bhopal | 01/21 04:30 | 29 | [212] Oliver Crawford v Bogdan Bobrov [410] | Walkover | |
| ITF M25 Bhopal | 01/20 06:45 | 28 | [212] Oliver Crawford v Eric Vanshelboim [393] | 6-1,6-7,6-4 | |
| ITF M25 Bhopal | 01/19 04:30 | 27 | Oliver Crawford v Aryan Shah | 6-3,6-4 | |
| ITF M25 Bhopal | 01/18 07:05 | 26 | Oliver Crawford v Mitsuki Wei Kang Leong | 6-3,3-6,6-1 | |
| ITF M25 Bhopal | 01/17 04:30 | 25 | Oliver Crawford v Karan Singh | 6-7,6-4,6-2 | |
| Australian Open | 01/12 00:40 | 19 | [213] Oliver Crawford v Vit Kopriva [132] | 4-6,4-6 | |
| Australian Open | 01/11 02:55 | 15 | [195] Francesco Passaro v Oliver Crawford [213] | 4-6,7-6,4-6 | |
| Australian Open | 01/09 23:00 | 14 | [213] Oliver Crawford v Ilya Ivashka [182] | 6-3,3-6,6-1 | |
| Challenger Brasilia | 11/21 19:45 | 25 | [295] Bernard Tomic v Oliver Crawford [207] | 6-3,6-2 | |
| Challenger Lima | 11/07 18:05 | 25 | [193] Oliver Crawford v Arklon H D P Cordova [192] | 5-7,0-6 | |
| Challenger Guayaquil | 10/31 19:00 | 25 | [193] Franco Agamenone v Oliver Crawford [196] | 6-3,4-6,6-1 | |
| Challenger Curitiba | 10/29 18:00 | 29 | [129] Hugo Dellien v Oliver Crawford [225] | 7-6,4-6,7-6 | |
| Challenger Curitiba | 10/29 13:00 | 28 | [154] Luciano Darderi v Oliver Crawford [225] | 2-6,3-6 | |
| Challenger Curitiba | 10/28 15:20 | 27 | [225] Oliver Crawford v Dalibor Svrcina [167] | 7-6,2-6,6-1 | |
| Challenger Curitiba | 10/27 20:00 | 26 | [144] Felipe M R Alves v Oliver Crawford [225] | 6-3,5-7,4-6 | |
| Challenger Curitiba | 10/24 19:25 | 25 | [225] Oliver Crawford v Juan Bautista Torres [348] | 6-1,6-3 | |
| Challenger Charleston | 10/01 15:00 | 29 | [263] Oliver Crawford v Abdullah Shelbayh [274] | 2-6,7-6,3-6 |