Simone Bolelli defeated Kevin Anderson 6-4 6-3 in the Madrid Masters round of 64 on clay. The result followed the form book — Simone Bolelli came in leading the head-to-head 1–0. Simone Bolelli extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-07-28 | Cincinnati Masters | R64 | hard | Simone Bolelli | 6-3 7-6(1) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.