Christian Dillschneider defeated Andrea Capodimonte 6-2 2-6 7-6 in the Italy 3 Masters 3 round of 32 on clay. The upset overturned the form book — Andrea Capodimonte came in leading the head-to-head 1–0. Christian Dillschneider claimed a first win over Andrea Capodimonte in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-28 | Switzerland 1 Masters 4 | R32 | clay | Andrea Capodimonte | 6-2 6-3 |