Markus Polessnig defeated Heiko Bollich 6-1 6-2 in the Italy 4 3 round of 32 on clay. The upset overturned the form book — Heiko Bollich came in leading the head-to-head 1–0, but Markus Polessnig had been the form player, winning 3 of their last 7 on clay. Markus Polessnig claimed a first win over Heiko Bollich in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-21 | Italy 4 4 | R16 | clay | Heiko Bollich | 6-1 7-6(6) |