Nicolas Kischkewitz defeated Stefano Cobolli 6-1 3-6 6-1 in the Italy 5 Masters 2 round of 16 on clay. Nicolas Kischkewitz extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-12 | Italy F3 | R32 | clay | Nicolas Kischkewitz | 6-2 6-3 |
| 1998-06-08 | Italy F9 | QF | clay | Nicolas Kischkewitz | 6-0 6-2 |
| 1997-06-28 | Italy 4 Masters 1 | F | clay | Stefano Cobolli | 7-6 6-2 |
| 1997-06-28 | Italy 4 Masters 4 | QF | clay | Stefano Cobolli | 6-2 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.