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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Gael Monfils | Miami Masters | 2005-03-21 | Miami Masters | 2025-03-17 | 7301d (20y 1d) |
| 2 |  Novak Djokovic | Cincinnati Masters | 2006-08-14 | Indian Wells Masters | 2026-03-08 | 7146d (19y 211d) |
| 3 |  Roger Federer | Stuttgart Masters | 2000-10-30 | Shanghai Masters | 2019-10-07 | 6916d (18y 346d) |
| 4 |  Feliciano Lopez | Madrid Masters | 2002-10-14 | Canada Masters | 2021-08-09 | 6874d (18y 304d) |
| 5 | Rafael Nadal | Indian Wells Masters | 2004-03-08 | Paris Masters | 2022-10-31 | 6811d (18y 241d) |
| 6 |  Andy Murray | Cincinnati Masters | 2005-08-15 | Miami Masters | 2024-03-18 | 6790d (18y 220d) |
| 7 |  Marin Cilic | Canada Masters | 2008-07-21 | Miami Masters | 2026-03-22 | 6453d (17y 248d) |
| 8 | Richard Gasquet | Canada Masters | 2005-08-08 | Paris Masters | 2022-10-31 | 6293d (17y 88d) |
| 9 | Gilles Simon | Cincinnati Masters | 2005-08-15 | Paris Masters | 2022-10-31 | 6286d (17y 81d) |
| 10 | Fabrice Santoro | Indian Wells Masters | 1991-03-04 | Miami Masters | 2008-03-27 | 6233d (17y 28d) |