| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-01-14 | Australian Open | R64 | hard | Novak Djokovic | 6-3 7-5 6-4 |
| 2016-08-29 | US Open | QF | hard | Novak Djokovic | 6-3 6-2 RET |
| 2016-03-07 | Indian Wells Masters | QF | hard | Novak Djokovic | 7-6(2) 7-6(2) |
| 2015-10-11 | Shanghai Masters | F | hard | Novak Djokovic | 6-2 6-4 |
| 2014-08-04 | Canada Masters | R16 | hard | Jo-Wilfried Tsonga | 6-2 6-2 |
| 2014-06-23 | Wimbledon | R16 | grass | Novak Djokovic | 6-3 6-4 7-6(5) |
| 2014-05-26 | Roland Garros | R16 | clay | Novak Djokovic | 6-1 6-4 6-1 |
| 2013-10-07 | Shanghai Masters | SF | hard | Novak Djokovic | 6-2 7-5 |
| 2013-03-07 | Indian Wells Masters | QF | hard | Novak Djokovic | 6-3 6-1 |
| 2012-11-05 | Tour Finals | RR | hard | Novak Djokovic | 7-6(4) 6-3 |
| 2012-10-01 | Beijing | F | hard | Novak Djokovic | 7-6(4) 6-2 |
| 2012-05-27 | Roland Garros | QF | clay | Novak Djokovic | 6-1 5-7 5-7 7-6(6) 6-1 |
| 2012-05-13 | Rome Masters | QF | clay | Novak Djokovic | 7-5 6-1 |
| 2011-11-07 | Paris Masters | QF | hard | Jo-Wilfried Tsonga | W/O |
| 2011-08-08 | Canada Masters | SF | hard | Novak Djokovic | 6-4 3-0 RET |
| 2011-06-20 | Wimbledon | SF | grass | Novak Djokovic | 7-6(4) 6-2 6-7(9) 6-3 |
| 2010-01-18 | Australian Open | QF | hard | Jo-Wilfried Tsonga | 7-6(8) 6-7(5) 1-6 6-3 6-1 |
| 2009-03-25 | Miami Masters | QF | hard | Novak Djokovic | 6-3 6-4 |
| 2009-02-16 | Marseille | SF | hard | Jo-Wilfried Tsonga | 6-4 7-6(1) |
| 2008-11-09 | Masters Cup | RR | hard | Jo-Wilfried Tsonga | 1-6 7-5 6-1 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.