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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Richard Gasquet | Monte Carlo Masters | 2002-04-15 | Monte Carlo Masters | 2025-04-07 | 8393d (22y 363d) |
| 2 | Gael Monfils | Paris Masters | 2004-11-01 | Madrid Masters | 2026-04-23 | 7843d (21y 178d) |
| 3 |  Rafael Nadal | Monte Carlo Masters | 2003-04-14 | Rome Masters | 2024-05-06 | 7693d (21y 28d) |
| 4 |  Stan Wawrinka | Rome Masters | 2005-05-02 | Monte Carlo | 2026-04-06 | 7644d (20y 344d) |
| 5 |  Novak Djokovic | Cincinnati Masters | 2005-08-15 | Indian Wells Masters | 2026-03-09 | 7511d (20y 211d) |
| 6 | Roger Federer | Miami Masters | 1999-03-15 | Shanghai Masters | 2019-10-07 | 7511d (20y 211d) |
| 7 |  Tommy Haas | Miami Masters | 1997-03-17 | Rome Masters | 2017-05-15 | 7364d (20y 64d) |
| 8 | Philipp Kohlschreiber | Hamburg Masters | 2002-05-13 | Indian Wells Masters | 2022-03-07 | 7238d (19y 303d) |
| 9 | Fabrice Santoro | Miami Masters | 1990-03-16 | Paris Masters | 2009-11-08 | 7177d (19y 242d) |
| 10 | Feliciano Lopez | Miami Masters | 2002-03-18 | Indian Wells Masters | 2021-10-04 | 7140d (19y 205d) |
| 11 | Fernando Verdasco | Miami Masters | 2003-03-17 | Miami Masters | 2022-03-21 | 6944d (19y 9d) |
| 12 |  Fabio Fognini | Rome Masters | 2006-05-08 | Rome Masters | 2025-05-05 | 6937d (19y 2d) |
| 13 |  Andy Murray | Cincinnati Masters | 2005-08-15 | Miami Masters | 2024-03-18 | 6790d (18y 220d) |
| 14 |  Marin Cilic | Indian Wells Masters | 2008-03-13 | Madrid Masters | 2026-04-22 | 6614d (18y 44d) |
| 15 | Adrian Mannarino | Paris Masters | 2008-10-26 | Madrid Masters | 2026-04-22 | 6387d (17y 182d) |
| 16 | Jo-Wilfried Tsonga | Paris Masters | 2004-11-01 | Monte Carlo Masters | 2022-04-11 | 6370d (17y 165d) |
| 17 |  Kei Nishikori | Indian Wells Masters | 2008-03-13 | Cincinnati Masters | 2025-08-07 | 6356d (17y 151d) |
| 18 |  Mikhail Youzhny | Monte Carlo Masters | 2001-04-16 | Canada Masters | 2018-08-06 | 6321d (17y 116d) |
| 19 | Gilles Simon | Cincinnati Masters | 2005-08-15 | Paris Masters | 2022-10-31 | 6286d (17y 81d) |
| 20 |  Lleyton Hewitt | Indian Wells Masters | 1998-03-09 | Miami Masters | 2015-03-25 | 6225d (17y 20d) |