Tiago Boschmans defeated Tomas Almeida 4-6 7-5 10-5 in the M25 Vale do Lobo 2 q32 on hard. The upset overturned the form book — Tomas Almeida came in leading the head-to-head 1–0. Tiago Boschmans claimed a first win over Tomas Almeida in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2023-09-03 | M25 Sintra 1 | Q64 | hard | Tomas Almeida | 6-4 3-6 10-8 |