Rui Machado defeated Roberto Menendez 5-7 6-4 6-0 in the Spain F32 qualifying round on clay. The upset overturned the form book — Roberto Menendez came in leading the head-to-head 2–0. Rui Machado claimed a first win over Roberto Menendez in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-07-05 | Spain F13 | R32 | clay | Roberto Menendez | 7-6(4) 6-2 |
| 2003-08-25 | Spain F20 | R16 | clay | Roberto Menendez | 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.