Alessandro Da Col defeated Adrian Menendez Maceiras 7-6 2-6 7-6 in the Spain F28 semi-final on hard. The upset overturned the form book — Adrian Menendez Maceiras came in leading the head-to-head 1–0. Alessandro Da Col claimed a first win over Adrian Menendez Maceiras in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-03-20 | Portugal F2 | R32 | hard | Adrian Menendez Maceiras | 5-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.