
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2024-12-30 | Brisbane | R16 | hard | Novak Djokovic | 6-3 6-3 |
| 2023-08-14 | Cincinnati Masters | R16 | hard | Novak Djokovic | 6-3 6-2 |
| 2022-05-02 | Madrid Masters | R32 | clay | Novak Djokovic | 6-3 6-2 |
| 2021-11-01 | Paris Masters | R16 | hard | Novak Djokovic | W/O |
| 2020-02-24 | Dubai | SF | hard | Novak Djokovic | 2-6 7-6(8) 6-1 |
| 2020-01-06 | Atp Cup | RR | hard | Novak Djokovic | 6-3 6-2 |
| 2018-01-15 | Australian Open | R64 | hard | Novak Djokovic | 4-6 6-3 6-1 6-3 |
| 2017-06-26 | Eastbourne | F | grass | Novak Djokovic | 6-3 6-4 |
| 2016-08-29 | US Open | SF | hard | Novak Djokovic | 6-3 6-2 3-6 6-2 |
| 2014-10-27 | Paris Masters | R16 | hard | Novak Djokovic | 6-3 7-6(2) |
| 2014-08-04 | Canada Masters | R32 | hard | Novak Djokovic | 6-2 6-7(4) 7-6(2) |
| 2013-10-07 | Shanghai Masters | QF | hard | Novak Djokovic | 6-7(4) 6-2 6-4 |
| 2011-08-14 | Cincinnati Masters | QF | hard | Novak Djokovic | 3-6 6-4 6-3 |
| 2011-08-08 | Canada Masters | QF | hard | Novak Djokovic | 6-2 6-1 |
| 2010-12-03 | Davis Cup WG F: SRB vs FRA | RR | hard | Novak Djokovic | 6-2 6-2 6-4 |
| 2010-08-30 | US Open | QF | hard | Novak Djokovic | 7-6(2) 6-1 6-2 |
| 2009-11-08 | Paris Masters | F | hard | Novak Djokovic | 6-2 5-7 7-6(3) |
| 2008-08-11 | Beijing Olympics | QF | hard | Novak Djokovic | 4-6 6-1 6-4 |
| 2006-05-29 | Roland Garros | R16 | clay | Novak Djokovic | 7-6(5) 7-6(5) 6-3 |
| 2005-08-29 | US Open | R128 | hard | Novak Djokovic | 7-5 4-6 7-6(5) 0-6 7-5 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.