| 5‑Mar‑2025 | Indian Wells Masters | Hard | R16 | 33 | 12 | (11)Ben Shelton [USA] d. (32)Nakashima | 7-6(6) 6-1 | | 0.68 | 0.0% | 1.6% | 48.4% | 60.0% | 53.1% | 2/5 | 1:34 |
| 26‑Aug‑2024 | US Open | Hard | R16 | 50 | 4 | (4)Alexander Zverev [GER] d. Nakashima | 3-6 6-1 6-2 6-2 | | 0.48 | 5.2% | 1.7% | 61.7% | 63.4% | 40.9% | 12/18 | 2:36 |
| 12‑Aug‑2024 | Cincinnati Masters | Hard | R16 | 49 | 6 | (6)Andrey Rublev [RUS] d. (WC)Nakashima | 7-6(5) 6-1 | | 0.66 | 7.5% | 1.9% | 47.2% | 76.0% | 57.1% | 2/4 | 1:21 |
| 27‑May‑2024 | Roland Garros | Clay | R64 | 84 | 8 | (8)Hubert Hurkacz [POL] d. Nakashima | 6-7(2) 6-1 6-3 7-6(5) | | 0.78 | 11.7% | 1.5% | 64.2% | 71.6% | 49.0% | 7/11 | |
| 22‑May‑2023 | Lyon | Clay | R16 | 52 | 78 | (8)Nakashima d. Arthur Rinderknech [FRA] | 7-6(6) 1-6 7-5 | | 0.98 | 6.0% | 3.0% | 62.0% | 71.0% | 57.9% | 8/11 | 2:42 |
| 29‑Aug‑2022 | US Open | Hard | R32 | 69 | 13 | (11)Jannik Sinner [ITA] d. Nakashima | 3-6 6-4 6-1 6-2 | (ch) | 0.79 | 2.5% | 2.5% | 58.5% | 62.3% | 44.9% | 13/19 | 2:59 |
| 6‑Jun‑2022 | s Hertogenbosch | Grass | QF | 64 | 70 | Adrian Mannarino [FRA] d. Nakashima | 6-7(5) 6-1 6-4 | | 0.71 | 11.1% | 2.2% | 74.4% | 74.6% | 34.8% | 3/6 | 2:03 |
| 27‑Sep‑2021 | San Diego | Hard | R16 | 83 | 5 | (1)Andrey Rublev [RUS] d. (WC)Nakashima | 6-2 6-1 | | 0.63 | 9.6% | 3.8% | 65.4% | 58.8% | 11.1% | 5/11 | 1:02 |
| 31‑Aug‑2020 | US Open | Hard | R64 | 223 | 7 | (5)Alexander Zverev [GER] d. Nakashima | 7-5 6-7(8) 6-3 6-1 | | 0.77 | 3.6% | 2.9% | 58.4% | 65.0% | 59.6% | 5/10 | 2:55 |
