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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Novak Djokovic | Indian Wells Masters | 2007-03-05 | Shanghai | 2025-09-24 | 6778d (18y 208d) |
| 2 |  Roger Federer | Miami Masters | 2002-03-18 | Miami Masters | 2019-03-18 | 6209d (17y 4d) |
| 3 |  Rafael Nadal | Miami Masters | 2005-03-21 | Indian Wells Masters | 2022-03-07 | 6195d (16y 355d) |
| 4 |  Tommy Haas | Hamburg Masters | 1997-05-05 | Miami Masters | 2013-03-20 | 5798d (15y 323d) |
| 5 |  Andre Agassi | Indian Wells Masters | 1990-03-05 | Canada Masters | 2005-08-08 | 5635d (15y 160d) |
| 6 |  Richard Gasquet | Monte Carlo Masters | 2005-04-11 | Cincinnati Masters | 2019-08-12 | 5236d (14y 126d) |
| 7 | Gael Monfils | Rome Masters | 2006-05-08 | Canada Masters | 2019-08-05 | 4837d (13y 92d) |
| 8 | David Ferrer | Miami Masters | 2005-03-21 | Cincinnati Masters | 2017-08-14 | 4529d (12y 149d) |
| 9 | Pete Sampras | Canada Masters | 1990-07-23 | Indian Wells Masters | 2002-03-11 | 4249d (11y 234d) |
| 10 |  Grigor Dimitrov | Rome Masters | 2014-05-11 | Miami Masters | 2025-03-17 | 3963d (10y 313d) |