Massimo Dellacqua defeated Paolo Cannova 6-2 6-4 in the Italy 3 Masters 4 round of 32 on clay. The result followed the form book — Massimo Dellacqua came in leading the head-to-head 2–0. Massimo Dellacqua extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-21 | Italy 3 Masters 4 | R16 | clay | Massimo Dellacqua | 6-1 6-7 6-2 |
| 1999-07-26 | Italy F14 | R16 | clay | Massimo Dellacqua | 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.