Rodrigo Monte defeated Federico Luzzi 4-6 7-5 6-2 in the Italy 2 Masters 2 qualifying round on clay. The upset overturned the form book — Federico Luzzi came in leading the head-to-head 2–0. Rodrigo Monte claimed a first win over Federico Luzzi in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | Italy F15 | R32 | clay | Federico Luzzi | 6-4 6-1 |
| 1999-06-19 | Italy 2 Masters 1 | R16 | clay | Federico Luzzi | 6-0 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.