Florian Allgauer defeated Nicolas Kischkewitz 2-6 6-1 6-1 in the Italy 4 Masters 2 qualifying round on clay. The upset overturned the form book — Nicolas Kischkewitz came in leading the head-to-head 4–2. Florian Allgauer narrowed the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-17 | Italy F8 | QF | clay | Florian Allgauer | 6-2 6-2 |
| 1999-04-26 | Italy F5 | SF | clay | Florian Allgauer | 6-1 3-1 |
| 1999-02-13 | Italy 1 Masters 1 | QF | clay | Nicolas Kischkewitz | 6-3 1-6 7-5 |
| 1999-02-13 | Italy 1 Masters 2 | R16 | clay | Nicolas Kischkewitz | 6-3 7-5 |
| 1997-06-28 | Italy 4 Masters 1 | R16 | clay | Nicolas Kischkewitz | 7-5 6-3 |
| 1997-06-28 | Italy 4 Masters 4 | R32 | clay | Nicolas Kischkewitz | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.