Pablo Santos defeated Rui Machado 6-2 6-1 in the Tunisia F2 qualifying round on clay. The upset overturned the form book — Rui Machado came in leading the head-to-head 2–1. Pablo Santos 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 |
| 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.