Gianluca Luddi defeated Gregor Krusic 6-3 7-6 in the Croatia 1 Masters 4 round of 32 on clay. The upset overturned the form book — Gregor Krusic came in leading the head-to-head 1–0, but Gianluca Luddi had been the form player, winning 6 of their last 10 on clay. Gianluca Luddi claimed a first win over Gregor Krusic in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-17 | Italy F8 | R32 | clay | Gregor Krusic | 6-3 2-6 6-3 |