Pablo Cuevas defeated Gilles Simon 6-4 7-6 in the Hamburg qualifying round 2 on clay. The upset overturned the form book — Gilles Simon came in leading the head-to-head 3–1. Pablo Cuevas narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2020-09-21 | Hamburg | Q2 | clay | Pablo Cuevas | 6-4 7-6(2) |
| 2020-01-20 | Australian Open | R128 | hard | Gilles Simon | 6-1 6-3 6-3 |
| 2013-05-27 | Roland Garros | R64 | clay | Gilles Simon | 6-7(2) 6-1 6-1 6-1 |
| 2011-03-23 | Miami Masters | R32 | hard | Gilles Simon | 4-6 6-1 6-2 |
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 (105 vs 113). ATP, WTA & Challenger.