Philipp Kohlschreiber advanced when Janko Tipsarevic retired 2-2 in the Canada Masters round of 64. Philipp Kohlschreiber narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-10-10 | Shanghai Masters | R64 | hard | Janko Tipsarevic | 6-2 6-4 |
| 2012-08-27 | US Open | R16 | hard | Janko Tipsarevic | 6-3 7-6(5) 6-2 |
| 2012-05-21 | Dusseldorf | RR | clay | Janko Tipsarevic | 6-4 3-6 7-5 |
| 2011-05-15 | Dusseldorf | RR | clay | Philipp Kohlschreiber | 6-4 7-6(5) |
| 2009-05-17 | Dusseldorf | F | clay | Janko Tipsarevic | 6-2 6-4 |
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