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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Rafael Nadal | Monte Carlo Masters | 2003-04-14 | Madrid Masters | 2024-04-22 | 7679d (21y 14d) |
| 2 |  Novak Djokovic | Paris Masters | 2005-10-31 | Indian Wells Masters | 2026-03-09 | 7434d (20y 134d) |
| 3 |  Gael Monfils | Miami Masters | 2005-03-21 | Miami Masters | 2025-03-17 | 7301d (20y 1d) |
| 4 |  Roger Federer | Miami Masters | 2001-03-19 | Shanghai Masters | 2019-10-07 | 6776d (18y 206d) |
| 5 |  Tommy Haas | Hamburg Masters | 1997-05-05 | Rome Masters | 2014-05-11 | 6215d (17y 10d) |
| 6 |  Andy Murray | Canada Masters | 2006-08-07 | Canada Masters | 2023-08-07 | 6209d (17y 4d) |
| 7 | Stan Wawrinka | Cincinnati Masters | 2006-08-14 | Cincinnati Masters | 2023-08-14 | 6209d (17y 4d) |
| 8 | Fabrice Santoro | Indian Wells Masters | 1991-03-04 | Paris Masters | 2007-10-28 | 6082d (16y 242d) |
| 9 | Gilles Simon | Monte Carlo Masters | 2006-04-17 | Paris Masters | 2022-10-31 | 6041d (16y 201d) |
| 10 |  Andre Agassi | Indian Wells Masters | 1990-03-05 | Canada Masters | 2005-08-08 | 5635d (15y 160d) |