Juan Monaco defeated Grigor Dimitrov 6-2 6-1 in the Tokyo round of 32 on hard. The result followed the form book — Juan Monaco came in leading the head-to-head 2–1, defending last year's round of 32. Juan Monaco extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2013-07-08 | Bastad | QF | clay | Grigor Dimitrov | 6-3 6-2 |
| 2012-10-29 | Paris Masters | R32 | hard | Juan Monaco | 7-6(4) 6-2 |
| 2011-04-18 | Barcelona | R64 | clay | Juan Monaco | 6-4 6-1 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.