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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 | Indian Wells Masters | 2026-03-05 | 7794d (21y 129d) |
| 3 |  Rafael Nadal | Monte Carlo Masters | 2003-04-14 | Rome Masters | 2024-05-06 | 7693d (21y 28d) |
| 4 |  Novak Djokovic | Cincinnati Masters | 2005-08-15 | Indian Wells Masters | 2026-03-09 | 7511d (20y 211d) |
| 5 |  Roger Federer | Miami Masters | 1999-03-15 | Shanghai Masters | 2019-10-07 | 7511d (20y 211d) |
| 6 | Stan Wawrinka | Rome Masters | 2005-05-02 | Shanghai | 2025-09-24 | 7450d (20y 150d) |
| 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) |