Heiko Bollich defeated Markus Polessnig 6-1 7-6 in the Italy 4 4 round of 16 on clay. The upset overturned the form book — Markus Polessnig came in leading the head-to-head 1–0. Heiko Bollich claimed a first win over Markus Polessnig in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-21 | Italy 4 3 | R32 | clay | Markus Polessnig | 6-1 6-2 |