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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Roger Federer | Hamburg Masters | 2002-05-13 | Miami Masters | 2019-03-18 | 6153d (16y 313d) |
| 2 |  Novak Djokovic | Miami Masters | 2007-03-19 | Paris Masters | 2023-10-30 | 6069d (16y 229d) |
| 3 |  Rafael Nadal | Monte Carlo Masters | 2005-04-11 | Rome Masters | 2021-05-08 | 5871d (16y 31d) |
| 4 |  Andre Agassi | Miami Masters | 1990-03-16 | Cincinnati Masters | 2004-08-02 | 5253d (14y 143d) |
| 5 |  Andy Murray | Cincinnati Masters | 2008-07-28 | Paris Masters | 2016-10-31 | 3017d (8y 97d) |
| 6 | Pete Sampras | Cincinnati Masters | 1992-08-10 | Miami Masters | 2000-03-20 | 2779d (7y 224d) |
| 7 |  Alexander Zverev | Rome Masters | 2017-05-15 | Paris Masters | 2024-10-28 | 2723d (7y 168d) |
| 8 |  Thomas Muster | Rome Masters | 1990-05-14 | Miami Masters | 1997-03-17 | 2499d (6y 309d) |
| 9 | Andy Roddick | Canada Masters | 2003-08-04 | Miami Masters | 2010-03-24 | 2424d (6y 234d) |
| 10 | Michael Chang | Canada Masters | 1990-07-23 | Indian Wells Masters | 1997-03-10 | 2422d (6y 232d) |