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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 |  Gael Monfils | Rome Masters | 2006-05-08 | Canada Masters | 2023-08-07 | 6300d (17y 95d) |
| 4 |  Rafael Nadal | Miami Masters | 2005-03-21 | Madrid Masters | 2022-05-02 | 6251d (17y 46d) |
| 5 |  Tommy Haas | Hamburg Masters | 1997-05-05 | Rome Masters | 2014-05-11 | 6215d (17y 10d) |
| 6 |  Andre Agassi | Indian Wells Masters | 1990-03-05 | Canada Masters | 2005-08-08 | 5635d (15y 160d) |
| 7 | Richard Gasquet | Monte Carlo Masters | 2005-04-11 | Cincinnati Masters | 2019-08-12 | 5236d (14y 126d) |
| 8 | Fernando Verdasco | Rome Masters | 2005-05-02 | Rome Masters | 2019-05-13 | 5124d (14y 14d) |
| 9 | David Ferrer | Hamburg Masters | 2004-05-10 | Cincinnati Masters | 2017-08-14 | 4844d (13y 99d) |
| 10 | Fabrice Santoro | Rome Masters | 1991-05-13 | Cincinnati Masters | 2004-08-02 | 4830d (13y 85d) |