Rui Machado defeated Pablo Santos 6-4 6-4 in the Spain F16 qualifying round on clay. The upset overturned the form book — Pablo Santos came in leading the head-to-head 2–1. Rui Machado narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-02-13 | Spain F6 | R32 | clay | Pablo Santos | 6-1 6-3 |
| 2005-11-21 | Spain F33 | R16 | clay | Rui Machado | 4-6 6-4 6-2 |
| 2004-06-14 | Tunisia F2 | QF | clay | Pablo Santos | 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.