

Novak Djokovic advanced when Daniil Medvedev retired 4-6 7-6 0-0 in the Astana semi-final. Novak Djokovic extended the head-to-head to 10–5.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2023-08-28 | US Open | F | hard | Novak Djokovic | 6-3 7-6 6-3 |
| 2023-02-27 | Dubai | SF | hard | Daniil Medvedev | 6-4 6-4 |
| 2023-01-02 | Adelaide 1 | SF | hard | Novak Djokovic | 6-3 6-4 |
| 2022-11-14 | Tour Finals | RR | hard | Novak Djokovic | 6-3 6-7 7-6 |
| 2021-11-01 | Paris Masters | F | hard | Novak Djokovic | 4-6 6-3 6-3 |
| 2021-08-30 | US Open | F | hard | Daniil Medvedev | 6-4 6-4 6-4 |
| 2021-02-08 | Australian Open | F | hard | Novak Djokovic | 7-5 6-2 6-2 |
| 2020-11-16 | Tour Finals | RR | hard | Daniil Medvedev | 6-3 6-3 |
| 2020-01-06 | Atp Cup | SF | hard | Novak Djokovic | 6-1 5-7 6-4 |
| 2019-08-12 | Cincinnati Masters | SF | hard | Daniil Medvedev | 3-6 6-3 6-3 |
| 2019-04-15 | Monte Carlo Masters | QF | clay | Daniil Medvedev | 6-3 4-6 6-2 |
| 2019-01-14 | Australian Open | R16 | hard | Novak Djokovic | 6-4 6-7 6-2 6-3 |
| 2017-06-26 | Eastbourne | SF | grass | Novak Djokovic | 6-4 6-4 |
| 2017-02-03 | Davis Cup WG R1: RUS vs SRB | RR | hard | Novak Djokovic | 3-6 6-4 6-1 1-0 |
Averages over each player's completed matches in the selected window (200 vs 198). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Djokovic N.: 12 days rest · 1 match (14d) · Medvedev D.: 19 days rest. Higher means fresher. About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Per-surface Serve / Return Rating (0–100, percentile within the hard field, opponent-adjusted over 52 weeks). About