Russell Henderson defeated Afonso Portugal 2-6 6-2 10-5 in the M25 Sintra 2 q32 on hard. The result followed the form book — Russell Henderson came in leading the head-to-head 2–0. Russell Henderson extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2024-03-10 | M25 Vale do Lobo 1 | Q32 | hard | Russell Henderson | 2-6 7-6(4) 10-7 |
| 2019-09-22 | M25+H Oliveira De Azemeis 1 | Q32 | hard | Russell Henderson | 5-3 |