Russell Henderson advanced when Afonso Portugal retired 5-3 in the M25+H Oliveira De Azemeis 1 q32. 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 |
| 2022-09-11 | M25 Sintra 2 | Q32 | hard | Russell Henderson | 2-6 6-2 10-5 |