Melle Van Gemerden defeated Daniel Caracciolo 6-3 6-2 in the Netherlands Masters 2 round of 16 on clay. The upset overturned the form book — Daniel Caracciolo came in leading the head-to-head 2–1. Melle Van Gemerden narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-28 | Switzerland 1 Masters 1 | F | clay | Daniel Caracciolo | 6-3 6-3 |
| 1999-08-28 | Switzerland 1 Masters 3 | QF | clay | Daniel Caracciolo | 6-2 5-7 7-6 |
| 1999-08-28 | Switzerland 1 Masters 4 | SF | clay | Melle Van Gemerden | 6-0 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.