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| Rank | Player | Age | Tournament |
|---|---|---|---|
| 1 | 40y 4d | Indian Wells Masters 2019 | |
| 2 | 39y 323d | Canada Masters 2021 | |
| 3 | 39y 192d | Miami Masters 1992 | |
| 4 | 39y 181d | Indian Wells Masters 1992 | |
| 5 | 39y 43d | Paris Masters 2020 | |
| 6 | 38y 197d | Miami Masters 2025 | |
| 7 | 38y 183d | Indian Wells Masters 2025 | |
| 8 | 38y 167d | Cincinnati Masters 2017 | |
| 9 | 38y 138d | Cincinnati Masters 2023 | |
| 10 | 38y 125d | Shanghai 2025 | |
| 11 | 38y 59d | Shanghai Masters 2019 | |
| 12 | 38y 31d | Shanghai Masters 2024 | |
| 13 | 38y 20d | Miami Masters 2017 | |
| 14 | 38y 3d | Cincinnati Masters 2019 | |
| 15 | 37y 345d | Cincinnati Masters 2024 | |
| 16 | 37y 342d | Indian Wells Masters 2023 | |
| 17 | 37y 307d | Paris Masters 2022 | |
| 18 | 37y 299d | Miami Masters 2025 | |
| 19 | 37y 245d | Paris Masters 2016 | |
| 20 | 37y 240d | Canada Masters 2016 |
