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| Rank | Player | Age | Tournament |
|---|---|---|---|
| 1 | 40y 165d | Cincinnati Masters 2019 | |
| 2 | 40y 9d | Monte Carlo Masters 2025 | |
| 3 | 40y 4d | Indian Wells Masters 2019 | |
| 4 | 39y 192d | Miami Masters 1992 | |
| 5 | 39y 188d | Shanghai Masters 2024 | |
| 6 | 39y 181d | Indian Wells Masters 1992 | |
| 7 | 39y 55d | Paris Masters 1991 | |
| 8 | 39y 48d | Stockholm Masters 1991 | |
| 9 | 39y 43d | Paris Masters 2020 | |
| 10 | 39y 42d | Rome Masters 2017 | |
| 11 | 39y 35d | Madrid Masters 2017 | |
| 12 | 39y 14d | Monte Carlo Masters 2017 | |
| 13 | 39y 11d | Monte Carlo Masters 2024 | |
| 14 | 38y 293d | Monte Carlo Masters 2025 | |
| 15 | 38y 232d | Madrid Masters 2025 | |
| 16 | 38y 223d | Shanghai Masters 2017 | |
| 17 | 38y 218d | Monte Carlo Masters 2025 | |
| 18 | 38y 215d | Paris Masters 2023 | |
| 19 | 38y 197d | Miami Masters 2025 | |
| 20 | 38y 193d | Miami Masters 1991 |
