Milos Raonic defeated Juan Monaco 6-3 6-4 in the Madrid Masters round of 32 on clay. The upset overturned the form book — Juan Monaco came in leading the head-to-head 2–0, defending last year's round of 32. Milos Raonic claimed a first win over Juan Monaco in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2014-10-05 | Shanghai Masters | R32 | hard | Juan Monaco | 5-2 RET |
| 2012-05-27 | Roland Garros | R32 | clay | Juan Monaco | 6-7(5) 6-3 6-7(5) 6-3 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.