| 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 | |
| Challenger Charleston | 09/30 15:00 | 28 | [414] Ernesto Escobedo v Oliver Crawford [263] | Retired | |
| Challenger Charleston | 09/29 15:00 | 27 | Oliver Crawford v Stefan Dostanic | 6-1,6-2 | |
| Challenger Charleston | 09/28 14:00 | 26 | [263] Oliver Crawford v Laurent Lokoli [225] | 7-6,6-2 | |
| Challenger Charleston | 09/27 15:35 | 25 | [200] Tennys Sandgren v Oliver Crawford [263] | 5-7,2-6 | |
| ITF M25 Kigali | 09/17 09:30 | 29 | [286] Oliver Crawford v Corentin Denolly [483] | 6-1,4-6,4-6 | |
| ITF M25 Kigali | 09/16 09:30 | 28 | Oliver Crawford v Guy Orly Iradukunda | 6-1,6-0 | |
| ITF M25 Kigali | 09/15 09:40 | 27 | Oliver Crawford v Vadym Ursu | 6-2,6-2 | |
| ITF M25 Kigali | 09/14 08:40 | 26 | Oliver Crawford v Abraham Asaba | 6-4,6-1 | |
| ITF M25 Kigali | 09/13 09:45 | 25 | Oliver Crawford v Raghav Jaisinghani | 6-2,6-1 | |
| ITF M25 Kigali | 09/10 08:55 | 29 | [294] Oliver Crawford v Damien Wenger [408] | 4-6,2-6 | |
| ITF M25 Kigali | 09/09 10:40 | 28 | Oliver Crawford v Vadym Ursu | 6-4,6-4 | |
| ITF M25 Kigali | 09/08 08:00 | 27 | Oliver Crawford v Rishab Agarwal | 6-0,6-2 | |
| ITF M25 Kigali | 09/07 08:35 | 26 | Oliver Crawford v Sai K R Ganta | 6-2,6-3 | |
| ITF M25 Kigali | 09/06 10:25 | 25 | Oliver Crawford v Arjun Mahadevan | 6-0,6-1 | |
| ITF M25 Oldenzaal | 09/03 13:10 | 29 | [294] Oliver Crawford v Lucas Gerch [383] | 5-7,0-6 | |
| ITF M25 Oldenzaal | 09/02 12:20 | 28 | Oliver Crawford v Mats Rosenkranz | 6-3,6-4 | |
| ITF M25 Oldenzaal | 09/01 11:15 | 27 | Oliver Crawford v Aleksandr Braynin | 6-1,6-4 | |
| ITF M25 Oldenzaal | 08/31 15:20 | 26 | Oliver Crawford v Stijn Slump | 6-4,6-2 | |
| ITF M25 Oldenzaal | 08/30 17:35 | 25 | Oliver Crawford v Thiemo De Bakker | 3-6,6-1,6-3 | |
| Challenger Augsburg | 08/23 08:00 | 26 | [294] Oliver Crawford v Carlos Taberner [361] | 6-3,4-6,6-7 | |
| Challenger Augsburg | 08/22 08:00 | 25 | [294] Oliver Crawford v Giovanni Fonio [288] | 6-2,6-3 | |
| ITF M25 Kramsach | 07/29 11:00 | 28 | Oliver Crawford v Gerard Campana Lee | 6-7,3-6 | |
| ITF M25 Kramsach | 07/28 09:00 | 27 | Oliver Crawford v Peter Heller | 6-3,6-4 | |
| ITF M25 Kramsach | 07/27 09:00 | 26 | Oliver Crawford v Hynek Barton | 7-6,3-6,6-4 | |
| ITF M25 Kramsach | 07/26 10:30 | 25 | Oliver Crawford v Dario Huber | 6-3,6-4 | |
| ITF M25 Gandia | 07/23 16:00 | 29 | Oliver Crawford v Sergi Perez Contri | 3-6,5-7 | |
| ITF M25 Gandia | 07/22 15:30 | 28 | Oliver Crawford v Pedro Rodenas | 6-3,6-3 |