Oliver Crawford defeated M. Mbithi 7-5 6-4 in the M25 Pensacola 1 round of 32 on clay. The result followed the form book — Oliver Crawford came in leading the head-to-head 1–0. Oliver Crawford extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2023-05-18 | M25 Kursumlijska Banja 2 | R16 | clay | Oliver Crawford | 6-0 6-2 |