Juan Monaco defeated Jurgen Melzer 6-7 7-5 6-2 in the Shanghai Masters quarter-final on hard. The result followed the form book — Juan Monaco came in leading the head-to-head 6–1, defending last year's round of 64. Juan Monaco extended the head-to-head to 7–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2014-05-04 | Madrid Masters | R64 | clay | Juan Monaco | 6-4 6-3 |
| 2013-08-11 | Cincinnati Masters | R64 | hard | Juan Monaco | 6-3 6-2 |
| 2010-10-04 | Tokyo | R32 | hard | Jurgen Melzer | 6-4 4-6 6-1 |
| 2007-05-28 | Roland Garros | R64 | clay | Juan Monaco | 6-2 6-3 6-2 |
| 2007-05-20 | Poertschach | R32 | clay | Juan Monaco | 6-3 6-1 |
| 2006-07-31 | Sopot | R32 | clay | Juan Monaco | 2-6 7-6(2) 6-4 |
| 2006-07-17 | Stuttgart | R16 | grass | Juan Monaco | 6-4 6-7(3) 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.