Holger Fischer defeated Simone Bolelli 6-1 6-3 in the Italy F3 round of 32 on hard. The upset overturned the form book — Simone Bolelli came in leading the head-to-head 2–0. Holger Fischer claimed a first win over Simone Bolelli in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-05-17 | Italy F8 | R16 | clay | Simone Bolelli | 5-7 6-2 7-5 |
| 2004-02-09 | Switzerland 1 1 | QF | carpet | Simone Bolelli | 7-6(2) 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.