Josh Reid defeated Maceo Simpson 6-2 6-2 in the M15 Monastir 40 q64 on hard. The upset overturned the form book — Maceo Simpson came in leading the head-to-head 1–0. Josh Reid claimed a first win over Maceo Simpson in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-11-28 | M15 Monastir 46 | Q64 | hard | Maceo Simpson | 6-3 6-3 |