| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-05-13 | Rome Masters | QF | clay | Novak Djokovic | 4-6 7-6(6) 6-4 |
| 2018-08-27 | US Open | F | hard | Novak Djokovic | 6-3 7-6(4) 6-3 |
| 2017-05-15 | Rome Masters | QF | clay | Novak Djokovic | 6-1 6-4 |
| 2017-03-06 | Indian Wells Masters | R32 | hard | Novak Djokovic | 7-5 4-6 6-1 |
| 2017-02-27 | Acapulco | R16 | hard | Novak Djokovic | 4-6 6-4 6-4 |
| 2016-08-08 | Rio Olympics | R64 | hard | Juan Martin del Potro | 7-6(4) 7-6(2) |
| 2013-11-04 | Tour Finals | RR | hard | Novak Djokovic | 6-3 3-6 6-3 |
| 2013-10-07 | Shanghai Masters | F | hard | Novak Djokovic | 6-1 3-6 7-6(3) |
| 2013-03-07 | Indian Wells Masters | SF | hard | Juan Martin del Potro | 4-6 6-4 6-4 |
| 2013-02-25 | Dubai | SF | hard | Novak Djokovic | 6-3 7-6(4) |
| 2012-11-05 | Tour Finals | SF | hard | Novak Djokovic | 4-6 6-3 6-2 |
| 2012-08-27 | US Open | QF | hard | Novak Djokovic | 6-2 7-6(3) 6-4 |
| 2012-08-12 | Cincinnati Masters | SF | hard | Novak Djokovic | 6-3 6-2 |
| 2012-07-25 | London Olympics | BR | grass | Juan Martin del Potro | 7-5 6-4 |
| 2011-09-16 | Davis Cup WG SF: SRB vs ARG | RR | hard | Juan Martin del Potro | 7-6(5) 3-0 RET |
| 2011-05-22 | Roland Garros | R32 | clay | Novak Djokovic | 6-3 3-6 6-3 6-2 |
| 2009-04-27 | Rome Masters | QF | clay | Novak Djokovic | 6-3 6-4 |
| 2008-11-09 | Masters Cup | RR | hard | Novak Djokovic | 7-5 6-3 |
| 2007-08-27 | US Open | R32 | hard | Novak Djokovic | 6-1 6-3 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.