Rafael Moreno Negrin defeated Adrian Menendez Maceiras 2-6 6-3 7-6 in the Spain F32 round of 16 on hard. The upset overturned the form book — Adrian Menendez Maceiras came in leading the head-to-head 1–0. Rafael Moreno Negrin 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 |
|---|---|---|---|---|---|
| 2004-09-06 | Spain F22 | R16 | hard | Adrian Menendez Maceiras | 6-4 1-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.