
Kyle Edmund defeated Novak Djokovic 6-3 2-6 6-3 in the Madrid Masters round of 32 on clay. The upset overturned the form book — Novak Djokovic came in ranked #4, leading the head-to-head 6–0, defending last year's semi-final. Kyle Edmund claimed a first win over Novak Djokovic in seven meetings, narrowing the head-to-head to 6–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2020-08-31 | US Open | R64 | hard | Novak Djokovic | 6-7(5) 6-3 6-4 6-2 |
| 2019-10-28 | Paris Masters | R16 | hard | Novak Djokovic | 7-6(7) 6-1 |
| 2018-07-02 | Wimbledon | R32 | grass | Novak Djokovic | 4-6 6-3 6-2 6-4 |
| 2017-03-06 | Indian Wells Masters | R64 | hard | Novak Djokovic | 6-4 7-6(5) |
| 2016-08-29 | US Open | R16 | hard | Novak Djokovic | 6-2 6-1 6-4 |
| 2016-03-21 | Miami Masters | R64 | hard | Novak Djokovic | 6-3 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.