Juan Monaco defeated Gilles Simon 6-4 6-0 in the Paris Masters round of 32 on hard. The upset overturned the form book — Gilles Simon came in leading the head-to-head 4–2, defending last year's round of 32. Juan Monaco narrowed the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-03-21 | Miami Masters | R64 | hard | Gilles Simon | 7-5 6-1 |
| 2013-04-05 | Davis Cup WG QF: ARG vs FRA | RR | clay | Juan Monaco | 7-6(2) 6-2 6-4 |
| 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 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.