Massimo Dellacqua defeated Federico Luzzi 6-0 5-7 6-4 in the Italy 3 Masters 4 qualifying round on clay. The upset overturned the form book — Federico Luzzi came in leading the head-to-head 3–1. Massimo Dellacqua narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-27 | Italy F17 | R16 | hard | Massimo Dellacqua | 6-4 6-4 |
| 1999-08-21 | Italy 3 Masters 1 | R32 | clay | Federico Luzzi | 6-4 6-2 |
| 1999-07-26 | Italy F14 | SF | clay | Federico Luzzi | 7-6 2-6 6-2 |
| 1999-06-19 | Italy 2 Masters 3 | R16 | clay | Federico Luzzi | 6-4 4-6 6-2 |
Averages over each player's completed matches in the selected window (6 vs 44). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About