Novak Djokovic leads the record after 20 meetings.
| Surface | Nishikori | Djokovic |
|---|---|---|
| Hard | 2 | 11 |
| Clay | 0 | 6 |
| Grass | 0 | 1 |
| Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|
| U.S. Open - New York 2021 | R3 | Hard | Djokovic | 6-7(4) 6-3 6-3 6-2 |
| Olympics - Tokyo 2021 | QF | Hard | Djokovic | 6-2 6-0 |
| Australian Open - Melbourne 2019 | QF | Hard | Djokovic | 6-1 4-1 ret. |
| U.S. Open - New York 2018 | SF | Hard | Djokovic | 6-3 6-4 6-2 |
| Wimbledon - London 2018 | QF | Grass | Djokovic | 6-3 3-6 6-2 6-2 |
| Internazionali BNL d'Italia - Rome 2018 | QF | Clay | Djokovic | 2-6 6-1 6-3 |
| Mutua Madrid Open - Madrid 2018 | R1 | Clay | Djokovic | 7-5 6-4 |
| Barclays ATP World Tour Finals - London 2016 | SF | Hard (Indoor) | Djokovic | 6-1 6-1 |
| Rogers Cup - Toronto 2016 | F | Hard | Djokovic | 6-3 7-5 |
| Internazionali BNL d'Italia - Rome 2016 | SF | Clay | Djokovic | 2-6 6-4 7-6(5) |
| Mutua Madrid Open - Madrid 2016 | SF | Clay | Djokovic | 6-3 7-6(4) |
| Miami Open - Miami 2016 | F | Hard | Djokovic | 6-3 6-3 |
| Australian Open - Melbourne 2016 | QF | Hard | Djokovic | 6-3 6-2 6-4 |
| Barclays ATP World Tour Finals - London 2015 | R5 | Hard (Indoor) | Djokovic | 6-1 6-1 |
| Internazionali BNL d'Italia - Rome 2015 | QF | Clay | Djokovic | 6-3 3-6 6-1 |
| Barclays ATP World Tour Finals - London 2014 | SF | Hard (Indoor) | Djokovic | 6-1 3-6 6-0 |
| BNP Paribas Masters - Paris 2014 | SF | Hard (Indoor) | Djokovic | 6-2 6-3 |
| U.S. Open - New York 2014 | SF | Hard | Nishikori | 6-4 1-6 7-6(4) 6-3 |
| Swiss Indoors Basel - Basel 2011 | SF | Hard (Indoor) | Nishikori | 2-6 7-6(4) 6-0 |
| French Open - Paris 2010 | R2 | Clay | Djokovic | 6-1 6-4 6-4 |
Meetings are the ones on our record. Older matches may be missing.
Match Point Challenge runs a prediction game on every ATP tournament. Free to play, no gambling.