Nicolas Kischkewitz defeated Marco Monnecchi 7-5 6-3 in the Italy 5 Masters 2 round of 32 on clay. The result followed the form book — Nicolas Kischkewitz came in leading the head-to-head 3–1. Nicolas Kischkewitz extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-19 | Italy 2 Masters 1 | R32 | clay | Marco Monnecchi | 6-2 6-3 |
| 1997-06-28 | Italy 4 Masters 4 | R16 | clay | Nicolas Kischkewitz | 7-6 1-6 6-2 |
| 1996-08-03 | Italy 4 Masters 2 | R32 | clay | Nicolas Kischkewitz | 6-4 6-7 6-2 |
| 1996-06-29 | Italy 3 Masters 1 | R16 | clay | Nicolas Kischkewitz | 6-2 6-4 |