Juan Monaco defeated Andy Murray 6-2 3-6 6-2 in the Valencia round of 16 on hard. The upset overturned the form book — Andy Murray came in leading the head-to-head 5–1, defending the title. Juan Monaco narrowed the head-to-head to 5–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-08-15 | Cincinnati Masters | R32 | hard | Andy Murray | 6-3 6-2 |
| 2016-08-08 | Rio Olympics | R32 | hard | Andy Murray | 6-3 6-1 |
| 2014-09-22 | Shenzhen | SF | hard | Andy Murray | 2-6 6-3 6-0 |
| 2010-10-10 | Shanghai Masters | SF | hard | Andy Murray | 6-4 6-1 |
| 2009-04-27 | Rome Masters | R32 | clay | Juan Monaco | 1-6 6-3 7-5 |
| 2009-03-25 | Miami Masters | R64 | hard | Andy Murray | 4-6 6-3 6-2 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.