Nicolas Lapentti defeated Radek Stepanek 6-3 1-6 6-3 in the Monte Carlo Masters round of 64 on clay. The upset overturned the form book — Radek Stepanek came in leading the head-to-head 3–0, defending last year's round of 64. Nicolas Lapentti claimed a first win over Radek Stepanek in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-01-19 | Australian Open | R128 | hard | Radek Stepanek | 3-6 6-3 6-4 6-4 |
| 2005-08-29 | US Open | R128 | hard | Radek Stepanek | 7-5 7-6(5) 6-1 |
| 2002-04-29 | Munich | QF | clay | Radek Stepanek | 7-6(5) 6-2 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.