Rui Machado defeated Pablo Santos 4-6 6-4 6-2 in the Spain F33 round of 16 on clay. The upset overturned the form book — Pablo Santos came in leading the head-to-head 3–2. Rui Machado narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-02-20 | Spain F7 | R32 | clay | Pablo Santos | 6-3 6-4 |
| 2006-02-13 | Spain F6 | R32 | clay | Pablo Santos | 6-1 6-3 |
| 2005-11-28 | Spain F34 | R16 | clay | Rui Machado | 6-1 6-2 |
| 2004-06-14 | Tunisia F2 | QF | clay | Pablo Santos | 6-2 6-1 |
| 2003-07-28 | Spain F16 | QF | clay | Rui Machado | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.