Rui Machado defeated Todor Enev 6-2 6-4 in the Portugal 1 Satellite 3 final on hard. Rui Machado extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-04-02 | Casablanca | Q32 | clay | Rui Machado | 6-1 6-2 |
| 2002-11-18 | Vietnam F1 | R32 | hard | Todor Enev | 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.