

| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-10-01 | Shanghai Masters | R64 | hard | Novak Djokovic | 7-6(2) 6-4 |
| 2022-09-26 | Tel Aviv | F | hard | Novak Djokovic | 6-3 6-4 |
| 2021-12-03 | Davis Cup Finals SF: CRO vs SRB | RR | hard | Novak Djokovic | 6-4 6-2 |
| 2019-05-06 | Madrid Masters | QF | clay | Novak Djokovic | W/O |
| 2018-11-12 | Tour Finals | RR | hard | Novak Djokovic | 7-6(7) 6-2 |
| 2018-10-29 | Paris Masters | QF | hard | Novak Djokovic | 4-6 6-2 6-3 |
| 2018-08-13 | Cincinnati Masters | SF | hard | Novak Djokovic | 6-4 3-6 6-3 |
| 2018-06-18 | Queen's Club | F | grass | Marin Cilic | 5-7 7-6(4) 6-3 |
| 2016-10-31 | Paris Masters | QF | hard | Marin Cilic | 6-4 7-6(2) |
| 2015-08-31 | US Open | SF | hard | Novak Djokovic | 6-0 6-1 6-2 |
| 2015-06-29 | Wimbledon | QF | grass | Novak Djokovic | 6-4 6-4 6-4 |
| 2014-11-09 | Tour Finals | RR | hard | Novak Djokovic | 6-1 6-1 |
| 2014-06-23 | Wimbledon | QF | grass | Novak Djokovic | 6-1 3-6 6-7(4) 6-2 6-2 |
| 2014-05-26 | Roland Garros | R32 | clay | Novak Djokovic | 6-3 6-2 6-7(2) 6-4 |
| 2014-03-06 | Indian Wells Masters | R16 | hard | Novak Djokovic | 1-6 6-2 6-3 |
| 2012-08-12 | Cincinnati Masters | QF | hard | Novak Djokovic | 6-3 6-2 |
| 2011-08-08 | Canada Masters | R16 | hard | Novak Djokovic | 7-5 6-2 |
| 2010-07-09 | Davis Cup WG QF: CRO vs SRB | RR | hard | Novak Djokovic | 6-3 6-3 6-2 |
| 2009-10-05 | Beijing | F | hard | Novak Djokovic | 6-2 7-6(4) |
| 2009-02-23 | Dubai | QF | hard | Novak Djokovic | 6-3 6-4 |
Averages from each player's recent completed matches (20 vs 19). ATP, WTA & Challenger.