Robert Shelton defeated Adan Freire Da Silva 4-6 6-0 13-11 in the M25 Idanha-a-Nova 2 q32 on hard. The upset overturned the form book — Adan Freire Da Silva came in leading the head-to-head 1–0. Robert Shelton claimed a first win over Adan Freire Da Silva in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2022-07-26 | M15 Castelo Branco 1 | R32 | hard | Adan Freire Da Silva | 6-2 7-6(4) |