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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Rafael Nadal | Monte Carlo Masters | 2005-04-11 | Rome Masters | 2021-05-08 | 5871d (16y 31d) |
| 2 |  Novak Djokovic | Rome Masters | 2008-05-05 | Rome Masters | 2022-05-09 | 5117d (14y 7d) |
| 3 |  Roger Federer | Hamburg Masters | 2002-05-13 | Madrid Masters | 2012-05-06 | 3646d (9y 361d) |
| 4 |  Alexander Zverev | Rome Masters | 2017-05-15 | Rome Masters | 2024-05-06 | 2548d (6y 358d) |
| 5 | Carlos Moya | Monte Carlo Masters | 1998-04-20 | Rome Masters | 2004-05-03 | 2205d (6y 15d) |
| 6 |  Thomas Muster | Rome Masters | 1990-05-14 | Rome Masters | 1996-05-13 | 2191d (6y 1d) |
| 7 |  Andrei Medvedev | Monte Carlo Masters | 1994-04-18 | Hamburg Masters | 1997-05-05 | 1113d (3y 18d) |
| 8 | Carlos Alcaraz | Madrid Masters | 2022-05-02 | Rome Masters | 2025-05-05 | 1099d (3y 4d) |
| 9 |  Stefanos Tsitsipas | Monte Carlo Masters | 2021-04-12 | Monte Carlo Masters | 2024-04-08 | 1092d (2y 362d) |
| 10 |  Marcelo Rios | Monte Carlo Masters | 1997-04-21 | Hamburg Masters | 1999-05-03 | 742d (2y 12d) |