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| Rank | Player | Age | Tournament |
|---|---|---|---|
| 1 | 40y 191d | Miami Masters 1993 | |
| 2 | 40y 180d | Shanghai 2025 | |
| 3 | 40y 17d | Miami Masters 2019 | |
| 4 | 40y 13d | Indian Wells Masters 2021 | |
| 5 | 40y 4d | Indian Wells Masters 2019 | |
| 6 | 39y 188d | Shanghai Masters 2024 | |
| 7 | 39y 183d | Miami Masters 2021 | |
| 8 | 39y 97d | Miami Masters 2021 | |
| 9 | 39y 19d | Miami Masters 2018 | |
| 10 | 39y 5d | Indian Wells Masters 2018 | |
| 11 | 38y 351d | Miami Masters 2017 | |
| 12 | 38y 341d | Indian Wells Masters 2024 | |
| 13 | 38y 329d | Canada Masters 2025 | |
| 14 | 38y 197d | Miami Masters 2025 | |
| 15 | 38y 193d | Miami Masters 1991 | |
| 16 | 38y 187d | Shanghai Masters 2023 | |
| 17 | 38y 183d | Indian Wells Masters 2025 | |
| 18 | 38y 178d | Miami Masters 1991 | |
| 19 | 38y 142d | Indian Wells Masters 2022 | |
| 20 | 38y 126d | Miami Masters 2022 |
