Juan Monaco defeated Thiemo De Bakker 2-6 6-3 6-4 in the Shanghai Masters round of 32 on hard. The upset overturned the form book — Thiemo De Bakker came in leading the head-to-head 2–1. Juan Monaco narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2015-02-09 | Sao Paulo | R32 | clay | Thiemo De Bakker | 6-7(5) 7-6(4) 6-4 |
| 2010-08-15 | Cincinnati Masters | R64 | hard | Thiemo De Bakker | 6-4 6-7(5) 6-3 |
| 2009-03-06 | Davis Cup WG R1: ARG vs NED | RR | clay | Juan Monaco | 6-1 6-2 7-6(1) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.