Stefano Tarallo defeated Gianluca Luddi 6-3 6-1 in the Italy 2 Masters 2 round of 16 on clay. The upset overturned the form book — Gianluca Luddi came in leading the head-to-head 3–1. Stefano Tarallo narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-19 | Italy 2 Masters 1 | F | clay | Gianluca Luddi | 4-6 6-3 6-2 |
| 1999-06-19 | Italy 2 Masters 3 | QF | clay | Gianluca Luddi | 6-4 6-0 |
| 1998-08-03 | Italy F12 | R16 | clay | Stefano Tarallo | 6-3 6-4 |
| 1997-06-28 | Italy 4 Masters 4 | QF | clay | Gianluca Luddi | 6-2 1-6 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.