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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Novak Djokovic | Indian Wells Masters | 2007-03-05 | Miami Masters | 2025-03-17 | 6587d (18y 17d) |
| 2 |  Roger Federer | Miami Masters | 2002-03-18 | Miami Masters | 2019-03-18 | 6209d (17y 4d) |
| 3 |  Rafael Nadal | Miami Masters | 2005-03-21 | Indian Wells Masters | 2022-03-07 | 6195d (16y 355d) |
| 4 |  Andre Agassi | Indian Wells Masters | 1990-03-05 | Canada Masters | 2005-08-08 | 5635d (15y 160d) |
| 5 | Pete Sampras | Cincinnati Masters | 1991-08-05 | Indian Wells Masters | 2001-03-12 | 3507d (9y 222d) |
| 6 |  Tomas Berdych | Paris Masters | 2005-10-31 | Monte Carlo Masters | 2015-04-12 | 3450d (9y 165d) |
| 7 | Stan Wawrinka | Rome Masters | 2008-05-05 | Indian Wells Masters | 2017-03-06 | 3227d (8y 307d) |
| 8 |  Juan Martin del Potro | Canada Masters | 2009-08-10 | Indian Wells Masters | 2018-03-05 | 3129d (8y 209d) |
| 9 |  Andy Murray | Cincinnati Masters | 2008-07-28 | Paris Masters | 2016-10-31 | 3017d (8y 97d) |
| 10 | Mardy Fish | Cincinnati Masters | 2003-08-11 | Canada Masters | 2011-08-08 | 2919d (7y 364d) |