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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Richard Gasquet | Monte Carlo Masters | 2002-04-15 | Monte Carlo Masters | 2025-04-07 | 8393d (22y 363d) |
| 2 |  Rafael Nadal | Monte Carlo Masters | 2003-04-14 | Madrid Masters | 2024-04-22 | 7679d (21y 14d) |
| 3 |  Tommy Haas | Hamburg Masters | 1997-05-05 | Rome Masters | 2017-05-15 | 7315d (20y 15d) |
| 4 | Gael Monfils | Rome Masters | 2006-05-08 | Monte Carlo Masters | 2025-04-07 | 6909d (18y 339d) |
| 5 |  Novak Djokovic | Hamburg Masters | 2006-05-15 | Monte Carlo Masters | 2025-04-07 | 6902d (18y 332d) |
| 6 |  Roger Federer | Monte Carlo Masters | 2001-04-16 | Rome Masters | 2019-05-13 | 6601d (18y 31d) |
| 7 | Stan Wawrinka | Rome Masters | 2005-05-02 | Monte Carlo Masters | 2023-04-10 | 6552d (17y 347d) |
| 8 | Fabrice Santoro | Hamburg Masters | 1990-05-07 | Rome Masters | 2006-05-08 | 5845d (16y 5d) |
| 9 | David Ferrer | Rome Masters | 2003-05-05 | Madrid Masters | 2019-05-06 | 5845d (16y 5d) |
| 10 |  Andy Murray | Hamburg Masters | 2006-05-15 | Madrid Masters | 2022-05-02 | 5831d (15y 356d) |