Janko Tipsarevic advanced when Juan Monaco retired 6-2 in the Davis Cup WG SF: SRB vs ARG round robin. 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 |
| 2012-10-29 | Paris Masters | R16 | hard | Janko Tipsarevic | 6-3 3-6 6-3 |
| 2012-07-09 | Stuttgart | F | grass | Janko Tipsarevic | 6-4 5-7 6-3 |
| 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) |
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 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About