Janko Tipsarevic defeated Grigor Dimitrov 7-6 6-2 in the Miami Masters round of 16 on hard. Janko Tipsarevic extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-05-27 | Roland Garros | R128 | clay | Grigor Dimitrov | 6-3 6-0 3-6 6-7(4) 6-4 |
| 2019-01-14 | Australian Open | R128 | hard | Grigor Dimitrov | 4-6 6-3 6-1 6-4 |
| 2016-06-13 | Queen's Club | R32 | grass | Janko Tipsarevic | 7-6(6) 4-6 6-3 |
| 2013-04-14 | Monte Carlo Masters | R32 | clay | Grigor Dimitrov | 7-6(3) 6-1 |
| 2011-07-31 | Washington | R16 | hard | Janko Tipsarevic | 6-4 6-2 |
| 2011-06-12 | Eastbourne | QF | grass | Janko Tipsarevic | 6-3 7-6(2) |
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
Dimitrov G.: 7 days rest · 1 match, 54 games (7d). Higher means fresher. About