Jack Sock defeated Milos Raonic 0-6 6-4 7-6 in the Shanghai Masters round of 16 on hard. The upset overturned the form book — Milos Raonic came in leading the head-to-head 8–2, defending last year's round of 16. Jack Sock narrowed the head-to-head to 8–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-07-31 | Washington | QF | hard | Jack Sock | 7-5 6-4 |
| 2016-06-27 | Wimbledon | R32 | grass | Milos Raonic | 7-6(2) 6-4 7-6(1) |
| 2016-03-21 | Miami Masters | R32 | hard | Milos Raonic | 7-6(3) 6-4 |
| 2014-10-27 | Paris Masters | R32 | hard | Milos Raonic | 6-3 5-7 7-6(4) |
| 2014-08-04 | Canada Masters | R32 | hard | Milos Raonic | 4-6 7-6(2) 7-6(4) |
| 2014-07-28 | Washington | R32 | hard | Milos Raonic | 7-6(3) 7-6(3) |
| 2014-06-23 | Wimbledon | R64 | grass | Milos Raonic | 6-3 6-4 6-4 |
| 2014-03-19 | Miami Masters | R64 | hard | Milos Raonic | 6-4 7-6(1) |
| 2013-08-11 | Cincinnati Masters | R64 | hard | Milos Raonic | 3-6 6-4 6-3 |
| 2013-02-18 | Memphis | R32 | hard | Jack Sock | 6-3 5-7 7-5 |
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 (199 vs 200). ATP, WTA & Challenger.