Florent Serra defeated Juan Monaco 6-3 1-6 6-3 in the Estoril round of 16 on clay. The upset overturned the form book — Juan Monaco came in leading the head-to-head 3–1. Florent Serra narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-10-10 | Shanghai Masters | R64 | hard | Juan Monaco | 6-4 7-6(3) |
| 2008-06-09 | Warsaw | R16 | clay | Juan Monaco | 7-5 6-3 |
| 2006-02-20 | Costa Do Sauipe | R16 | hard | Juan Monaco | 6-1 6-1 |
| 2004-10-11 | Metz | R32 | hard | Florent Serra | 6-4 4-6 6-0 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (164 vs 200). ATP, WTA & Challenger.