Milos Raonic defeated Janko Tipsarevic 6-7 6-2 7-6 in the Tokyo quarter-final on hard. The result followed the form book — Milos Raonic came in leading the head-to-head 4–0, defending last year's round of 16. Milos Raonic extended the head-to-head to 5–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-05-23 | Roland Garros | R128 | clay | Milos Raonic | 6-3 6-2 7-6(5) |
| 2013-09-13 | Davis Cup WG SF: SRB vs CAN | RR | clay | Milos Raonic | 5-7 6-3 3-6 6-3 10-8 |
| 2013-08-11 | Cincinnati Masters | R32 | hard | Milos Raonic | 6-4 7-6(4) |
| 2012-01-02 | Chennai | F | hard | Milos Raonic | 6-7(4) 7-6(4) 7-6(4) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.