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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Novak Djokovic | Madrid Masters | 2006-10-16 | Shanghai | 2025-09-24 | 6918d (18y 348d) |
| 2 |  Roger Federer | Miami Masters | 2001-03-19 | Shanghai Masters | 2019-10-07 | 6776d (18y 206d) |
| 3 |  Rafael Nadal | Miami Masters | 2005-03-21 | Indian Wells Masters | 2022-03-07 | 6195d (16y 355d) |
| 4 |  Andre Agassi | Indian Wells Masters | 1990-03-05 | Canada Masters | 2005-08-08 | 5635d (15y 160d) |
| 5 |  Gael Monfils | Madrid Masters | 2008-10-12 | Canada Masters | 2023-08-07 | 5412d (14y 302d) |
| 6 | Richard Gasquet | Canada Masters | 2006-08-07 | Cincinnati Masters | 2019-08-12 | 4753d (13y 8d) |
| 7 |  Kei Nishikori | Shanghai Masters | 2011-10-09 | Canada Masters | 2024-08-06 | 4685d (12y 305d) |
| 8 | Stan Wawrinka | Indian Wells Masters | 2008-03-13 | Paris Masters | 2020-11-02 | 4617d (12y 237d) |
| 9 | David Ferrer | Miami Masters | 2005-03-21 | Cincinnati Masters | 2017-08-14 | 4529d (12y 149d) |
| 10 | Feliciano Lopez | Canada Masters | 2003-08-04 | Cincinnati Masters | 2015-08-16 | 4395d (12y 15d) |