Adan Freire Da Silva defeated Afonso Portugal 6-3 6-3 in the M25 Porto 1 round of 32 on hard. The result followed the form book — Adan Freire Da Silva came in leading the head-to-head 1–0. Adan Freire Da Silva extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2023-07-16 | M25 Castelo Branco 1 | Q32 | hard | Adan Freire Da Silva | 7-6(4) 6-3 |