Jo-Wilfried Tsonga defeated Milos Raonic 4-6 7-5 6-4 in the Indian Wells Masters round of 16 on hard. The upset overturned the form book — Milos Raonic came in leading the head-to-head 5–1, defending last year's round of 32. Jo-Wilfried Tsonga narrowed the head-to-head to 5–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-06-10 | Stuttgart | R16 | grass | Milos Raonic | 6-4 6-7(5) 7-6(1) |
| 2018-10-29 | Paris Masters | R64 | hard | Milos Raonic | 6-7(4) 7-6(5) 7-6(5) |
| 2016-10-31 | Paris Masters | QF | hard | Milos Raonic | 6-2 7-6(4) |
| 2016-05-02 | Madrid Masters | R16 | clay | Milos Raonic | 6-4 6-4 |
| 2014-05-11 | Rome Masters | R16 | clay | Milos Raonic | 7-6(5) 6-4 |
| 2012-07-25 | London Olympics | R32 | grass | Jo-Wilfried Tsonga | 6-3 3-6 25-23 |
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.