Rui Machado advanced when Pedro Leao retired 6-4 1-1 in the Portugal 2 4 round of 16. Rui Machado extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-05-05 | Portugal 1 1 | R16 | clay | Rui Machado | 6-4 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.