| 15‑Jan‑2024 | Australian Open | Hard | SF | 3 | 6 | (3)Medvedev d. (6)Alexander Zverev [GER] | 5-7 3-6 7-6(4) 7-6(5) 6-3 | (ch) | 1.01 | 9.0% | 3.8% | 60.3% | 76.6% | 56.5% | 5/10 | 4:18 |
| 13‑Nov‑2023 | Tour Finals | Hard | RR | 3 | 7 | (3)Medvedev d. (7)Alexander Zverev [GER] | 7-6(7) 6-4 | (ch) | 1.20 | 5.7% | 2.9% | 72.9% | 78.4% | 52.6% | 3/4 | 1:45 |
| 27‑Sep‑2023 | Beijing | Hard | SF | 3 | 10 | (2)Medvedev d. (8)Alexander Zverev [GER] | 6-4 6-3 | (ch) | 1.55 | 14.0% | 1.8% | 71.9% | 80.5% | 68.8% | 4/4 | 1:25 |
| 14‑Aug‑2023 | Cincinnati Masters | Hard | R16 | 3 | 17 | (16)Alexander Zverev [GER] d. (3)Medvedev | 6-4 5-7 6-4 | (ch) | 1.08 | 5.6% | 7.8% | 53.3% | 83.3% | 47.6% | 5/8 | 2:32 |
| 8‑May‑2023 | Rome Masters | Clay | R16 | 3 | 22 | (3)Medvedev d. (19)Alexander Zverev [GER] | 6-2 7-6(3) | (ch) | 1.45 | 2.9% | 4.4% | 64.7% | 81.8% | 50.0% | 2/3 | 1:56 |
| 10‑Apr‑2023 | Monte Carlo Masters | Clay | R16 | 5 | 16 | (3)Medvedev d. (13)Alexander Zverev [GER] | 3-6 7-5 7-6(7) | (ch) | 1.08 | 2.9% | 7.8% | 54.4% | 71.4% | 40.4% | 5/11 | 3:05 |
| 6‑Mar‑2023 | Indian Wells Masters | Hard | R16 | 6 | 14 | (5)Medvedev d. (12)Alexander Zverev [GER] | 6-7(5) 7-6(5) 7-5 | (ch) | 1.03 | 9.2% | 3.8% | 66.4% | 74.7% | 54.5% | 15/17 | 3:17 |
| 15‑Nov‑2021 | Tour Finals | Hard | F | 2 | 3 | (3)Alexander Zverev [GER] d. (2)Medvedev | 6-4 6-4 | (ch) | 0.70 | 5.2% | 3.4% | 58.6% | 73.5% | 54.2% | 2/4 | 1:15 |
| 15‑Nov‑2021 | Tour Finals | Hard | RR | 2 | 3 | (2)Medvedev d. (3)Alexander Zverev [GER] | 6-3 6-7(3) 7-6(6) | (ch) | 1.15 | 13.1% | 0.9% | 70.1% | 78.7% | 59.4% | 4/4 | 2:35 |
| 1‑Nov‑2021 | Paris Masters | Hard | SF | 2 | 4 | (2)Medvedev d. (4)Alexander Zverev [GER] | 6-2 6-2 | (ch) | 1.79 | 7.8% | 0.0% | 56.9% | 79.3% | 63.6% | 3/3 | 1:20 |
| 2‑Feb‑2021 | Atp Cup | Hard | SF | 4 | 7 | Medvedev d. Alexander Zverev [GER] | 3-6 6-3 7-5 | (ch) | 0.99 | 11.2% | 12.1% | 52.3% | 82.1% | 39.2% | 9/11 | 2:37 |
| 16‑Nov‑2020 | Tour Finals | Hard | RR | 4 | 7 | (4)Medvedev d. (5)Alexander Zverev [GER] | 6-3 6-4 | (ch) | 1.39 | 6.3% | 3.2% | 66.7% | 73.8% | 57.1% | 5/6 | 1:29 |
| 2‑Nov‑2020 | Paris Masters | Hard | F | 5 | 7 | (3)Medvedev d. (4)Alexander Zverev [GER] | 5-7 6-4 6-1 | (ch) | 1.42 | 16.9% | 2.4% | 57.8% | 79.2% | 60.0% | 6/7 | 2:07 |
| 11‑Nov‑2019 | Tour Finals | Hard | RR | 4 | 7 | (7)Alexander Zverev [GER] d. (4)Medvedev | 6-4 7-6(4) | (ch) | 0.95 | 16.7% | 3.3% | 66.7% | 77.5% | 75.0% | 1/2 | 1:18 |
| 7‑Oct‑2019 | Shanghai Masters | Hard | F | 4 | 6 | (3)Medvedev d. (5)Alexander Zverev [GER] | 6-4 6-1 | (ch) | 1.50 | 7.0% | 3.5% | 57.9% | 84.8% | 41.7% | 5/6 | 1:13 |
| 6‑Aug‑2018 | Canada Masters | Hard | R16 | 68 | 3 | (2)Alexander Zverev [GER] d. (Q)Medvedev | 6-3 6-2 | (ch) | 0.23 | 10.9% | 2.2% | 65.2% | 63.3% | 43.8% | 0/3 | 0:52 |
| 19‑Mar‑2018 | Miami Masters | Hard | R64 | 52 | 5 | (4)Alexander Zverev [GER] d. Medvedev | 6-4 1-6 7-6(5) | (ch) | 1.03 | 7.7% | 4.8% | 62.5% | 67.7% | 56.4% | 6/8 | 2:13 |
| 31‑Jul‑2017 | Washington | Hard | QF | 50 | 8 | (5)Alexander Zverev [GER] d. Medvedev | 6-2 6-4 | | 0.52 | 3.9% | 9.8% | 62.7% | 71.9% | 36.8% | 2/5 | 0:57 |
| 19‑Sep‑2016 | St. Petersburg | Hard | R16 | 144 | 27 | (5)Alexander Zverev [GER] d. (Q)Medvedev | 6-3 7-5 | | 0.69 | 6.3% | 5.0% | 55.0% | 61.4% | 36.1% | 4/9 | 1:25 |
