Jan Lennard Struff defeated Gilles Simon 6-1 6-1 in the Miami Masters round of 64 on hard. The upset overturned the form book — Gilles Simon came in leading the head-to-head 2–1, defending last year's quarter-final. Jan Lennard Struff narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-10-17 | Antwerp | R16 | hard | Jan Lennard Struff | 6-4 6-4 |
| 2016-06-06 | Stuttgart | R16 | grass | Gilles Simon | 6-4 4-6 6-2 |
| 2015-03-06 | Davis Cup WG R1: GER vs FRA | RR | hard | Gilles Simon | 7-6(4) 2-6 6-7(1) 6-2 10-8 |
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 200). ATP, WTA & Challenger.