Janko Tipsarevic defeated Juan Monaco 6-3 3-6 6-3 in the Paris Masters round of 16 on hard. The upset overturned the form book — Juan Monaco came in leading the head-to-head 3–2, defending last year's quarter-final. Janko Tipsarevic narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2013-05-05 | Madrid Masters | R64 | clay | Juan Monaco | 7-6(5) 6-3 |
| 2012-07-09 | Stuttgart | F | grass | Janko Tipsarevic | 6-4 5-7 6-3 |
| 2011-09-16 | Davis Cup WG SF: SRB vs ARG | RR | hard | Janko Tipsarevic | 6-2 RET |
| 2011-07-18 | Hamburg | R32 | clay | Juan Monaco | 6-2 6-4 |
| 2009-05-17 | Dusseldorf | RR | clay | Juan Monaco | 6-4 7-6(8) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.