| 2‑Oct‑2024 | Shanghai Masters | Hard | R16 | 12 | 5 | (5)Daniil Medvedev [RUS] d. (10)Tsitsipas | 7-6(3) 6-3 | (ch) | 0.60 | 4.8% | 4.8% | 62.7% | 71.2% | 41.9% | 9/11 | 1:50 |
| 23‑Oct‑2023 | Vienna | Hard | SF | 7 | 3 | (1)Daniil Medvedev [RUS] d. (4)Tsitsipas | 6-4 7-6(6) | (ch) | 0.80 | 8.5% | 2.8% | 59.2% | 78.6% | 58.6% | 4/5 | 1:44 |
| 8‑May‑2023 | Rome Masters | Clay | SF | 5 | 3 | (3)Daniil Medvedev [RUS] d. (5)Tsitsipas | 7-5 7-5 | (ch) | 0.82 | 4.3% | 4.3% | 55.1% | 71.1% | 48.4% | 0/4 | 1:47 |
| 14‑Nov‑2022 | Tour Finals | Hard | RR | 3 | 5 | (2)Tsitsipas d. (4)Daniil Medvedev [RUS] | 6-3 6-7(11) 7-6(1) | (ch) | 1.14 | 8.7% | 1.0% | 74.8% | 83.1% | 53.8% | 0/1 | 2:21 |
| 15‑Aug‑2022 | Cincinnati Masters | Hard | SF | 7 | 1 | (4)Tsitsipas d. (1)Daniil Medvedev [RUS] | 7-6(6) 3-6 6-3 | (ch) | 1.14 | 4.4% | 7.7% | 65.9% | 81.7% | 38.7% | 0/3 | 2:23 |
| 17‑Jan‑2022 | Australian Open | Hard | SF | 4 | 2 | (2)Daniil Medvedev [RUS] d. (4)Tsitsipas | 7-6(5) 4-6 6-4 6-1 | (ch) | 0.53 | 4.2% | 0.8% | 69.2% | 67.5% | 62.2% | 8/12 | 2:30 |
| 31‑May‑2021 | Roland Garros | Clay | QF | 5 | 2 | (5)Tsitsipas d. (2)Daniil Medvedev [RUS] | 6-3 7-6(3) 7-5 | (ch) | 1.52 | 2.9% | 1.0% | 64.7% | 72.7% | 75.0% | 6/8 | 2:19 |
| 8‑Feb‑2021 | Australian Open | Hard | SF | 6 | 4 | (4)Daniil Medvedev [RUS] d. (5)Tsitsipas | 6-4 6-2 7-5 | (ch) | 0.57 | 3.0% | 3.0% | 69.3% | 61.4% | 41.9% | 4/9 | 2:09 |
| 11‑Nov‑2019 | Tour Finals | Hard | RR | 6 | 4 | (6)Tsitsipas d. (4)Daniil Medvedev [RUS] | 7-6(5) 6-4 | (ch) | 1.12 | 6.8% | 0.0% | 60.3% | 88.6% | 41.4% | 0/0 | 1:42 |
| 7‑Oct‑2019 | Shanghai Masters | Hard | SF | 7 | 4 | (3)Daniil Medvedev [RUS] d. (6)Tsitsipas | 7-6(5) 7-5 | (ch) | 0.72 | 12.2% | 4.1% | 66.2% | 81.6% | 44.0% | 1/3 | 1:36 |
| 15‑Apr‑2019 | Monte Carlo Masters | Clay | R16 | 8 | 14 | (10)Daniil Medvedev [RUS] d. (6)Tsitsipas | 6-2 1-6 6-4 | (ch) | 0.92 | 2.6% | 2.6% | 69.2% | 68.5% | 37.5% | 4/8 | 1:45 |
| 22‑Oct‑2018 | Basel | Hard | QF | 16 | 20 | (7)Daniil Medvedev [RUS] d. (4)Tsitsipas | 6-4 3-6 6-3 | | 0.85 | 3.5% | 1.2% | 57.0% | 69.4% | 62.2% | 3/5 | 1:50 |
| 27‑Aug‑2018 | US Open | Hard | R64 | 15 | 36 | Daniil Medvedev [RUS] d. (15)Tsitsipas | 6-4 6-3 4-6 6-3 | | 0.64 | 3.6% | 5.4% | 49.1% | 72.7% | 47.4% | 6/12 | 2:48 |
| 19‑Mar‑2018 | Miami Masters | Hard | R128 | 70 | 52 | Daniil Medvedev [RUS] d. Tsitsipas | 2-6 6-4 6-2 | | 0.97 | 7.5% | 2.5% | 58.8% | 74.5% | 39.4% | 8/12 | 1:52 |
