John Isner defeated Milos Raonic 3-6 6-3 6-4 3-6 6-2 in the US Open round of 16 on hard. The result followed the form book — John Isner came in leading the head-to-head 4–1, defending last year's round of 32. John Isner extended the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2018-07-02 | Wimbledon | QF | grass | John Isner | 6-7(5) 7-6(7) 6-4 6-3 |
| 2016-08-15 | Cincinnati Masters | R32 | hard | Milos Raonic | 7-6(5) 7-6(5) |
| 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 144). ATP, WTA & Challenger.