Milos Raonic defeated John Isner 7-6 7-6 in the Cincinnati Masters round of 32 on hard. The upset overturned the form book — John Isner came in leading the head-to-head 5–0, defending last year's round of 64, but Milos Raonic had been the form player, winning 2 of their last 4 on hard. Milos Raonic claimed a first win over John Isner in six meetings, narrowing the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2018-08-27 | US Open | R16 | hard | John Isner | 3-6 6-3 6-4 3-6 6-2 |
| 2018-07-02 | Wimbledon | QF | grass | John Isner | 6-7(5) 7-6(7) 6-4 6-3 |
| 2015-03-25 | Miami Masters | R16 | hard | John Isner | 6-7(3) 7-6(6) 7-6(5) |
| 2013-08-11 | Cincinnati Masters | R16 | hard | John Isner | 7-6(5) 6-4 |
| 2012-08-06 | Canada Masters | QF | hard | John Isner | 7-6(9) 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.