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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Gael Monfils | Indian Wells Masters | 2005-03-07 | Madrid Masters | 2026-04-23 | 7717d (21y 52d) |
| 2 | Richard Gasquet | Miami Masters | 2003-03-17 | Madrid Masters | 2024-04-22 | 7707d (21y 42d) |
| 3 |  Rafael Nadal | Indian Wells Masters | 2004-03-08 | Rome Masters | 2024-05-06 | 7364d (20y 64d) |
| 4 |  Tommy Haas | Miami Masters | 1997-03-17 | Miami Masters | 2017-03-20 | 7308d (20y 8d) |
| 5 |  Stan Wawrinka | Indian Wells Masters | 2006-03-06 | Shanghai | 2025-09-24 | 7142d (19y 207d) |
| 6 | Feliciano Lopez | Miami Masters | 2002-03-18 | Indian Wells Masters | 2021-10-04 | 7140d (19y 205d) |
| 7 | Fabrice Santoro | Miami Masters | 1990-03-16 | Miami Masters | 2009-03-25 | 6949d (19y 14d) |
| 8 | Fernando Verdasco | Miami Masters | 2003-03-17 | Miami Masters | 2022-03-21 | 6944d (19y 9d) |
| 9 |  Marin Cilic | Indian Wells Masters | 2008-03-13 | Rome Masters | 2026-05-07 | 6629d (18y 59d) |
| 10 |  Andy Murray | Indian Wells Masters | 2006-03-06 | Miami Masters | 2024-03-18 | 6587d (18y 17d) |