Gilles Simon defeated Juan Monaco 7-5 6-1 in the Miami Masters round of 64 on hard. Gilles Simon extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2013-04-05 | Davis Cup WG QF: ARG vs FRA | RR | clay | Juan Monaco | 7-6(2) 6-2 6-4 |
| 2011-11-07 | Paris Masters | R32 | hard | Juan Monaco | 6-4 6-0 |
| 2008-10-20 | Lyon | R32 | clay | Gilles Simon | 2-6 6-4 6-1 |
| 2007-07-09 | Bastad | R16 | clay | Gilles Simon | 6-4 6-4 |
| 2006-09-11 | Bucharest | R32 | clay | Gilles Simon | 7-5 3-6 6-3 |
| 2005-04-04 | Casablanca | QF | clay | Juan Monaco | 4-6 6-2 7-5 |
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 (200 vs 33). ATP, WTA & Challenger.