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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Gael Monfils | Indian Wells Masters | 2005-03-07 | Indian Wells Masters | 2026-03-05 | 7668d (21y 3d) |
| 2 |  Novak Djokovic | Cincinnati Masters | 2005-08-15 | Indian Wells Masters | 2026-03-08 | 7510d (20y 210d) |
| 3 | Fabrice Santoro | Miami Masters | 1990-03-16 | Paris Masters | 2009-11-08 | 7177d (19y 242d) |
| 4 | Richard Gasquet | Canada Masters | 2005-08-08 | Paris Masters | 2024-10-28 | 7021d (19y 86d) |
| 5 |  Stan Wawrinka | Canada Masters | 2005-08-08 | Shanghai Masters | 2024-10-02 | 6995d (19y 60d) |
| 6 | Roger Federer | Miami Masters | 2000-03-20 | Miami Masters | 2019-03-18 | 6937d (19y 2d) |
| 7 |  Feliciano Lopez | Miami Masters | 2002-03-18 | Paris Masters | 2020-11-02 | 6804d (18y 234d) |
| 8 |  Andy Murray | Cincinnati Masters | 2005-08-15 | Miami Masters | 2024-03-18 | 6790d (18y 220d) |
| 9 |  Tommy Haas | Miami Masters | 1997-03-17 | Shanghai Masters | 2015-10-11 | 6782d (18y 212d) |
| 10 | Rafael Nadal | Madrid Masters | 2003-10-13 | Indian Wells Masters | 2022-03-07 | 6720d (18y 150d) |