Marco Chiudinelli defeated Alessandro Tombolini 7-6 7-5 in the Switzerland 3 Masters 2 qualifying round on carpet. The result followed the form book — Marco Chiudinelli came in leading the head-to-head 1–0. Marco Chiudinelli extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | Switzerland 2 Masters 3 | R16 | carpet | Marco Chiudinelli | 6-1 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.