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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Novak Djokovic | Miami Masters | 2007-03-19 | Paris Masters | 2023-10-30 | 6069d (16y 229d) |
| 2 |  Roger Federer | Indian Wells Masters | 2004-03-08 | Miami Masters | 2019-03-18 | 5488d (15y 13d) |
| 3 |  Andre Agassi | Miami Masters | 1990-03-16 | Cincinnati Masters | 2004-08-02 | 5253d (14y 143d) |
| 4 |  Rafael Nadal | Canada Masters | 2005-08-08 | Canada Masters | 2019-08-05 | 5110d (14y 0d) |
| 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 | Canada Masters | 2017-08-07 | Paris Masters | 2024-10-28 | 2639d (7y 84d) |
| 8 | Andy Roddick | Canada Masters | 2003-08-04 | Miami Masters | 2010-03-24 | 2424d (6y 234d) |
| 9 | Michael Chang | Canada Masters | 1990-07-23 | Indian Wells Masters | 1997-03-10 | 2422d (6y 232d) |
| 10 |  Jo-Wilfried Tsonga | Paris Masters | 2008-10-26 | Canada Masters | 2014-08-04 | 2108d (5y 283d) |