| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-08-07 | Canada Masters | R16 | hard | Roger Federer | 4-6 6-4 6-2 |
| 2014-08-10 | Cincinnati Masters | F | hard | Roger Federer | 6-3 1-6 6-2 |
| 2012-11-05 | Tour Finals | RR | hard | Roger Federer | 6-4 7-6(5) |
| 2012-05-06 | Madrid Masters | QF | clay | Roger Federer | 6-4 6-4 |
| 2011-11-20 | Tour Finals | SF | hard | Roger Federer | 7-5 6-3 |
| 2010-11-21 | Tour Finals | RR | hard | Roger Federer | 6-1 6-4 |
| 2010-05-09 | Madrid Masters | SF | clay | Roger Federer | 7-5 3-6 6-3 |
| 2009-08-16 | Cincinnati Masters | R16 | hard | Roger Federer | 3-6 6-3 6-4 |
| 2007-11-12 | Masters Cup | F | hard | Roger Federer | 6-2 6-3 6-2 |
| 2007-05-14 | Hamburg Masters | QF | clay | Roger Federer | 6-3 4-6 6-3 |
| 2007-04-15 | Monte Carlo Masters | QF | clay | Roger Federer | 6-4 6-0 |
| 2006-10-23 | Basel | QF | hard | Roger Federer | 6-3 7-6(14) |
| 2006-04-17 | Monte Carlo Masters | QF | clay | Roger Federer | 6-1 6-3 |
| 2006-03-20 | Miami Masters | SF | hard | Roger Federer | 6-1 6-4 |
| 2005-01-03 | Doha | R32 | hard | Roger Federer | 6-1 6-1 |
| 2003-10-06 | Vienna | R32 | hard | Roger Federer | 6-2 6-2 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.