Adan Freire Da Silva defeated Robert Shelton 6-2 7-6 in the M15 Castelo Branco 1 round of 32 on hard. The upset overturned the form book — Robert Shelton came in leading the head-to-head 1–0. Adan Freire Da Silva claimed a first win over Robert Shelton in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2022-07-17 | M25 Idanha-a-Nova 2 | Q32 | hard | Robert Shelton | 4-6 6-0 13-11 |