Filippo Messori defeated Tomas Cakl 6-4 6-1 in the Italy 5 3 semi-final on clay. Filippo Messori extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-11-20 | Spain F14 | QF | clay | Tomas Cakl | 6-3 6-1 |
| 2000-10-02 | Italy 5 1 | QF | clay | Filippo Messori | 1-6 6-3 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.