All meetings (23)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 2025-10-01 | ATP | Shanghai Masters | Round of 64 | Hard | Novak Djokovic | 7-62 | 6-4 | |||
| 2022-09-26 | ATP | Tel Aviv | Final | Hard | Novak Djokovic | 6-3 | 6-4 | |||
| 2021-12-03 | ATP | Davis Cup Finals SF: CRO vs SRB | Round Robin | Hard | Novak Djokovic | 6-4 | 6-2 | |||
| 2019-05-06 | ATP | Madrid Masters | Quarterfinal | Clay | Novak Djokovic | W/O | ||||
| 2018-11-12 | ATP | Tour Finals | Round Robin | Hard | Novak Djokovic | 7-67 | 6-2 | |||
| 2018-10-29 | ATP | Paris Masters | Quarterfinal | Hard | Novak Djokovic | 4-6 | 6-2 | 6-3 | ||
| 2018-08-13 | ATP | Cincinnati Masters | Semifinal | Hard | Novak Djokovic | 6-4 | 3-6 | 6-3 | ||
| 2018-06-18 | ATP | Queen's Club | Final | Grass | Marin Cilic | 7-5 | 6-74 | 3-6 | ||
| 2016-10-31 | ATP | Paris Masters | Quarterfinal | Hard | Marin Cilic | 4-6 | 6-72 | |||
| 2015-08-31 | ATP | US Open | Semifinal | Hard | Novak Djokovic | 6-0 | 6-1 | 6-2 | ||
| 2015-06-29 | ATP | Wimbledon | Quarterfinal | Grass | Novak Djokovic | 6-4 | 6-4 | 6-4 | ||
| 2015-04-12 | ATP | Monte Carlo Masters | Quarterfinal | Clay | Novak Djokovic | 6-0 | 6-3 | |||
| 2014-11-09 | ATP | Tour Finals | Round Robin | Hard | Novak Djokovic | 6-1 | 6-1 | |||
| 2014-06-23 | ATP | Wimbledon | Quarterfinal | Grass | Novak Djokovic | 6-1 | 3-6 | 6-74 | 6-2 | 6-2 |
| 2014-05-26 | ATP | Roland Garros | Round of 32 | Clay | Novak Djokovic | 6-3 | 6-2 | 6-72 | 6-4 | |
| 2014-03-06 | ATP | Indian Wells Masters | Round of 16 | Hard | Novak Djokovic | 1-6 | 6-2 | 6-3 | ||
| 2012-08-12 | ATP | Cincinnati Masters | Quarterfinal | Hard | Novak Djokovic | 6-3 | 6-2 | |||
| 2011-08-08 | ATP | Canada Masters | Round of 16 | Hard | Novak Djokovic | 7-5 | 6-2 | |||
| 2010-07-09 | ATP | Davis Cup WG QF: CRO vs SRB | Round Robin | Hard | Novak Djokovic | 6-3 | 6-3 | 6-2 | ||
| 2009-10-05 | ATP | Beijing | Final | Hard | Novak Djokovic | 6-2 | 7-64 | |||
| 2009-02-23 | ATP | Dubai | Quarterfinal | Hard | Novak Djokovic | 6-3 | 6-4 | |||
| 2008-08-25 | ATP | US Open | Round of 32 | Hard | Novak Djokovic | 6-77 | 7-5 | 6-4 | 7-60 | |
| 2008-03-03 | ATP | Dubai | Round of 32 | Hard | Novak Djokovic | 6-4 | 6-3 | |||