Jan Lennard Struff defeated Milos Raonic 7-6 7-6 in the Atp Cup round robin on hard. The upset overturned the form book — Milos Raonic came in leading the head-to-head 2–1. Jan Lennard Struff narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-03-04 | Indian Wells Masters | R16 | hard | Milos Raonic | 6-4 6-3 |
| 2019-02-25 | Dubai | R32 | hard | Jan Lennard Struff | 6-4 5-7 6-4 |
| 2017-07-03 | Wimbledon | R128 | grass | Milos Raonic | 7-6(5) 6-2 7-6(4) |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Per-surface Serve / Return Rating (0–100, percentile within the hard field, opponent-adjusted over 52 weeks). About
Averages over each player's completed matches in the selected window (200 vs 31). ATP, WTA & Challenger.