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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 | 6069 |
| 2 |  Roger Federer | Indian Wells Masters | 2004-03-08 | Miami Masters | 2019-03-18 | 5488 |
| 3 |  Andre Agassi | Miami Masters | 1990-03-16 | Cincinnati Masters | 2004-08-02 | 5253 |
| 4 |  Rafael Nadal | Canada Masters | 2005-08-08 | Canada Masters | 2019-08-05 | 5110 |
| 5 |  Andy Murray | Cincinnati Masters | 2008-07-28 | Paris Masters | 2016-10-31 | 3017 |
| 6 | Pete Sampras | Cincinnati Masters | 1992-08-10 | Miami Masters | 2000-03-20 | 2779 |
| 7 |  Alexander Zverev | Canada Masters | 2017-08-07 | Paris Masters | 2024-10-28 | 2639 |
| 8 | Andy Roddick | Canada Masters | 2003-08-04 | Miami Masters | 2010-03-24 | 2424 |
| 9 | Michael Chang | Canada Masters | 1990-07-23 | Indian Wells Masters | 1997-03-10 | 2422 |
| 10 |  Jo-Wilfried Tsonga | Paris Masters | 2008-10-26 | Canada Masters | 2014-08-04 | 2108 |
| 11 |  Marat Safin | Canada Masters | 2000-07-31 | Madrid Masters | 2004-10-18 | 1540 |
| 12 |  Wayne Ferreira | Canada Masters | 1996-08-19 | Stuttgart Masters | 2000-10-30 | 1533 |
| 13 | Daniil Medvedev | Cincinnati Masters | 2019-08-12 | Miami Masters | 2023-03-20 | 1316 |
| 14 | Carlos Alcaraz | Miami Masters | 2022-03-21 | Cincinnati Masters | 2025-08-07 | 1235 |
| 15 |  Hubert Hurkacz | Miami Masters | 2021-03-22 | Shanghai Masters | 2023-10-02 | 924 |
| 16 |  Jannik Sinner | Canada Masters | 2023-08-07 | Paris Masters | 2025-10-27 | 812 |
| 17 | Jim Courier | Indian Wells Masters | 1991-03-04 | Indian Wells Masters | 1993-03-01 | 728 |
| 18 | Nikolay Davydenko | Miami Masters | 2008-03-27 | Shanghai Masters | 2009-10-11 | 563 |
| 19 |  Lleyton Hewitt | Indian Wells Masters | 2002-03-11 | Indian Wells Masters | 2003-03-10 | 364 |
| 20 |  Thomas Enqvist | Stuttgart Masters | 1999-10-25 | Cincinnati Masters | 2000-08-07 | 287 |