Juan Monaco defeated Andreas Seppi 6-1 4-6 6-2 in the Rome Masters round of 64 on clay. The upset overturned the form book — Andreas Seppi came in leading the head-to-head 3–2, defending last year's round of 32. Juan Monaco narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2014-07-27 | Kitzbuhel | QF | clay | Juan Monaco | 6-2 3-6 6-3 |
| 2014-07-14 | Hamburg | R32 | clay | Andreas Seppi | 1-6 6-0 7-6(3) |
| 2014-05-26 | Roland Garros | R64 | clay | Andreas Seppi | 6-2 6-4 6-4 |
| 2011-08-29 | US Open | R128 | hard | Juan Monaco | 7-6(1) 6-2 6-2 |
| 2008-05-11 | Hamburg Masters | R16 | clay | Andreas Seppi | 6-0 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.