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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Richard Gasquet | Miami Masters | 2003-03-17 | Paris Masters | 2024-10-28 | 7896d (21y 231d) |
| 2 | Gael Monfils | Indian Wells Masters | 2005-03-07 | Indian Wells Masters | 2026-03-05 | 7668d (21y 3d) |
| 3 |  Roger Federer | Miami Masters | 1999-03-15 | Shanghai Masters | 2019-10-07 | 7511d (20y 211d) |
| 4 |  Novak Djokovic | Cincinnati Masters | 2005-08-15 | Indian Wells Masters | 2026-03-09 | 7511d (20y 211d) |
| 5 | Stan Wawrinka | Canada Masters | 2005-08-08 | Shanghai | 2025-09-24 | 7352d (20y 52d) |
| 6 |  Tommy Haas | Miami Masters | 1997-03-17 | Miami Masters | 2017-03-20 | 7308d (20y 8d) |
| 7 | Fabrice Santoro | Miami Masters | 1990-03-16 | Paris Masters | 2009-11-08 | 7177d (19y 242d) |
| 8 |  Feliciano Lopez | Miami Masters | 2002-03-18 | Indian Wells Masters | 2021-10-04 | 7140d (19y 205d) |
| 9 | Rafael Nadal | Madrid Masters | 2003-10-13 | Paris Masters | 2022-10-31 | 6958d (19y 23d) |
| 10 | Fernando Verdasco | Miami Masters | 2003-03-17 | Miami Masters | 2022-03-21 | 6944d (19y 9d) |