| 13‑Nov‑2023 | Tour Finals | Hard | RR | 3 | 5 | (3)Medvedev d. (5)Andrey Rublev [RUS] | 6-4 6-2 | (ch) | 1.46 | 15.6% | 4.7% | 56.3% | 83.3% | 50.0% | 7/7 | 1:31 |
| 28‑Aug‑2023 | US Open | Hard | QF | 3 | 8 | (3)Medvedev d. (8)Andrey Rublev [RUS] | 6-4 6-3 6-4 | (ch) | 1.09 | 8.0% | 9.0% | 55.0% | 74.5% | 28.9% | 8/13 | 2:48 |
| 27‑Feb‑2023 | Dubai | Hard | F | 7 | 6 | (3)Medvedev d. (2)Andrey Rublev [RUS] | 6-2 6-2 | (ch) | 2.50 | 22.5% | 2.5% | 72.5% | 82.8% | 72.7% | 0/0 | 1:08 |
| 14‑Nov‑2022 | Tour Finals | Hard | RR | 5 | 7 | (6)Andrey Rublev [RUS] d. (4)Medvedev | 6-7(7) 6-3 7-6(7) | (ch) | 0.75 | 19.5% | 6.5% | 66.7% | 79.3% | 43.9% | 6/9 | 2:31 |
| 16‑Aug‑2021 | Cincinnati Masters | Hard | SF | 2 | 7 | (4)Andrey Rublev [RUS] d. (1)Medvedev | 2-6 6-3 6-3 | (ch) | 0.92 | 8.0% | 3.0% | 54.0% | 66.7% | 47.8% | 6/10 | 2:21 |
| 8‑Feb‑2021 | Australian Open | Hard | QF | 4 | 8 | (4)Medvedev d. (7)Andrey Rublev [RUS] | 7-5 6-3 6-2 | (ch) | 1.32 | 15.6% | 4.4% | 60.0% | 79.6% | 52.8% | 4/5 | 2:05 |
| 31‑Aug‑2020 | US Open | Hard | QF | 5 | 14 | (3)Medvedev d. (10)Andrey Rublev [RUS] | 7-6(6) 6-3 7-6(5) | (ch) | 1.45 | 16.5% | 3.1% | 58.8% | 89.5% | 65.0% | 0/0 | 2:27 |
| 16‑Sep‑2019 | St. Petersburg | Hard | QF | 4 | 38 | (1)Medvedev d. (5)Andrey Rublev [RUS] | 6-4 7-5 | (ch) | 1.19 | 17.4% | 7.2% | 60.9% | 71.4% | 40.7% | 3/6 | 1:41 |
| 12‑Aug‑2019 | Cincinnati Masters | Hard | QF | 8 | 70 | (9)Medvedev d. (Q)Andrey Rublev [RUS] | 6-2 6-3 | | 1.53 | 17.6% | 3.9% | 54.9% | 75.0% | 56.5% | 0/1 | 1:01 |
| 24‑Oct‑2016 | Budapest CH | Hard | R16 | 106 | 167 | (5)Medvedev d. Andrey Rublev [RUS] | 6-3 6-2 | | 2.20 | 8.7% | 6.5% | 65.2% | 83.3% | 68.8% | 0/0 | 1:03 |
