Level, 1 wins each over 2 singles meetings since 2024. Last meeting on 25/04/2025 at Mutua Madrid Open - Madrid.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 25/04/2025 | Mutua Madrid Open - Madrid | Round 2 | clay | Shapovalov | 1-6 4-6 |
| 30/12/2024 | Hong Kong Tennis Open - Hong Kong | Round 1 | hard | Nishikori | 2-6 3-6 |
| clay | Nishikori 0 - 1 Shapovalov |
| hard | Nishikori 1 - 0 Shapovalov |
| 2025 | Nishikori 0 - 1 Shapovalov |
| 2024 | Nishikori 1 - 0 Shapovalov |
81 wins, 53 losses since 2021 (60.4%).
Last matches: D V V D V
154 wins, 123 losses since 2021 (55.6%).
Last matches: D V V V D
Level, 1 wins each over 2 singles meetings since 2024.
On 25/04/2025, at Mutua Madrid Open - Madrid (Round 2): Denis Shapovalov won 1-6 4-6.