Marcos Jimenez Letrado defeated Adrian Menendez Maceiras 6-4 7-6 in the Spain F16 qualifying round on clay. The upset overturned the form book — Adrian Menendez Maceiras came in leading the head-to-head 2–0. Marcos Jimenez Letrado claimed a first win over Adrian Menendez Maceiras in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-03-07 | Portugal F3 | R32 | hard | Adrian Menendez Maceiras | 7-5 1-0 |
| 2004-10-11 | Spain F27 | R16 | hard | Adrian Menendez Maceiras | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.