| 11‑Nov‑2024 | Tour Finals | Hard | RR | 4 | 1 | (1)Jannik Sinner [ITA] d. (4)Medvedev | 6-3 6-4 | (ch) | 0.58 | 11.5% | 0.0% | 63.5% | 72.7% | 42.1% | 2/5 | 1:13 |
| 2‑Oct‑2024 | Shanghai Masters | Hard | QF | 5 | 1 | (1)Jannik Sinner [ITA] d. (5)Medvedev | 6-1 6-4 | (ch) | 0.52 | 5.2% | 6.9% | 53.4% | 80.6% | 22.2% | 1/4 | 1:24 |
| 26‑Aug‑2024 | US Open | Hard | QF | 5 | 1 | (1)Jannik Sinner [ITA] d. (5)Medvedev | 6-2 1-6 6-1 6-4 | (ch) | 0.70 | 4.6% | 5.5% | 56.0% | 67.2% | 41.7% | 10/15 | 2:39 |
| 1‑Jul‑2024 | Wimbledon | Grass | QF | 5 | 1 | (5)Medvedev d. (1)Jannik Sinner [ITA] | 6-7(7) 6-4 7-6(4) 2-6 6-3 | (ch) | 0.88 | 8.6% | 6.3% | 68.4% | 76.5% | 45.5% | 3/6 | 4:00 |
| 18‑Mar‑2024 | Miami Masters | Hard | SF | 4 | 3 | (2)Jannik Sinner [ITA] d. (3)Medvedev | 6-1 6-2 | (ch) | 0.53 | 6.0% | 4.0% | 64.0% | 53.1% | 38.9% | 5/9 | 1:09 |
| 15‑Jan‑2024 | Australian Open | Hard | F | 3 | 4 | (4)Jannik Sinner [ITA] d. (3)Medvedev | 3-6 3-6 6-4 6-4 6-3 | (ch) | 1.01 | 7.9% | 2.2% | 68.3% | 75.8% | 45.5% | 5/9 | 3:44 |
| 13‑Nov‑2023 | Tour Finals | Hard | SF | 3 | 4 | (4)Jannik Sinner [ITA] d. (3)Medvedev | 6-3 6-7(4) 6-1 | (ch) | 0.87 | 11.4% | 2.3% | 62.5% | 80.0% | 36.4% | 4/7 | 2:29 |
| 23‑Oct‑2023 | Vienna | Hard | F | 3 | 4 | (2)Jannik Sinner [ITA] d. (1)Medvedev | 7-6(7) 4-6 6-3 | (ch) | 0.92 | 9.8% | 6.1% | 66.7% | 64.8% | 40.9% | 12/16 | 3:06 |
| 27‑Sep‑2023 | Beijing | Hard | F | 3 | 7 | (6)Jannik Sinner [ITA] d. (2)Medvedev | 7-6(2) 7-6(2) | (ch) | 0.69 | 7.7% | 5.1% | 73.1% | 75.4% | 52.4% | 5/5 | 2:01 |
| 20‑Mar‑2023 | Miami Masters | Hard | F | 5 | 11 | (4)Medvedev d. (10)Jannik Sinner [ITA] | 7-5 6-3 | (ch) | 1.58 | 14.3% | 9.5% | 58.7% | 86.5% | 46.2% | 4/6 | 1:34 |
| 13‑Feb‑2023 | Rotterdam | Hard | F | 11 | 14 | (6)Medvedev d. Jannik Sinner [ITA] | 5-7 6-2 6-2 | (ch) | 1.28 | 4.7% | 1.2% | 68.6% | 74.6% | 44.4% | 4/6 | 2:29 |
| 24‑Oct‑2022 | Vienna | Hard | QF | 4 | 12 | (1)Medvedev d. (6)Jannik Sinner [ITA] | 6-4 6-2 | (ch) | 1.64 | 14.3% | 0.0% | 75.5% | 81.1% | 50.0% | 0/0 | 1:30 |
| 15‑Nov‑2021 | Tour Finals | Hard | RR | 2 | 11 | (2)Medvedev d. (9)Jannik Sinner [ITA] | 6-0 6-7(5) 7-6(8) | (ch) | 1.29 | 17.6% | 4.9% | 70.6% | 76.4% | 60.0% | 3/5 | 2:29 |
| 8‑Mar‑2021 | Marseille | Hard | QF | 3 | 34 | (1)Medvedev d. (5)Jannik Sinner [ITA] | 6-2 6-4 | (ch) | 1.65 | 14.0% | 6.0% | 70.0% | 80.0% | 60.0% | 1/1 | 1:15 |
| 17‑Feb‑2020 | Marseille | Hard | R16 | 5 | 68 | (1)Medvedev d. Jannik Sinner [ITA] | 1-6 6-1 6-2 | (ch) | 1.79 | 12.1% | 1.7% | 50.0% | 79.3% | 69.0% | 0/2 | 1:19 |
