Pablo Cuevas defeated Jack Sock 6-7 6-4 6-0 in the Madrid Masters round of 64 on clay. Pablo Cuevas extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2020-08-31 | US Open | R128 | hard | Jack Sock | 3-6 6-4 6-2 4-6 7-6(2) |
| 2019-08-26 | US Open | R128 | hard | Pablo Cuevas | 6-4 7-5 7-6(5) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.