Nicolas Kischkewitz defeated Filippo Messori 6-2 6-0 in the Italy 6 Masters 2 round of 32 on clay. The upset overturned the form book — Filippo Messori came in leading the head-to-head 4–0. Nicolas Kischkewitz claimed a first win over Filippo Messori in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-04-14 | Italy F3 | QF | clay | Filippo Messori | 6-4 3-6 6-1 |
| 1995-07-29 | Italy 4 Masters 1 | R32 | clay | Filippo Messori | 6-0 3-6 6-4 |
| 1995-07-29 | Italy 4 Masters 3 | R16 | clay | Filippo Messori | 6-2 6-4 |
| 1995-07-29 | Italy 4 Masters 4 | QF | clay | Filippo Messori | 7-5 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.