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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Richard Gasquet | Monte Carlo Masters | 2002-04-15 | Monte Carlo Masters | 2025-04-07 | 8393d (22y 363d) |
| 2 |  Rafael Nadal | Monte Carlo Masters | 2003-04-14 | Rome Masters | 2024-05-06 | 7693d (21y 28d) |
| 3 | Gael Monfils | Monte Carlo Masters | 2005-04-11 | Monte Carlo | 2026-04-05 | 7664d (20y 364d) |
| 4 |  Stan Wawrinka | Rome Masters | 2005-05-02 | Monte Carlo | 2026-04-06 | 7644d (20y 344d) |
| 5 |  Novak Djokovic | Monte Carlo Masters | 2006-04-17 | Rome Masters | 2026-05-08 | 7326d (20y 26d) |
| 6 |  Tommy Haas | Hamburg Masters | 1997-05-05 | Rome Masters | 2017-05-15 | 7315d (20y 15d) |
| 7 |  Fabio Fognini | Rome Masters | 2006-05-08 | Monte Carlo Masters | 2025-04-07 | 6909d (18y 339d) |
| 8 |  Marin Cilic | Monte Carlo Masters | 2008-04-20 | Rome Masters | 2026-05-07 | 6591d (18y 21d) |
| 9 | Fabrice Santoro | Monte Carlo Masters | 1990-04-23 | Rome Masters | 2008-05-05 | 6587d (18y 17d) |
| 10 | Philipp Kohlschreiber | Hamburg Masters | 2002-05-13 | Rome Masters | 2019-05-13 | 6209d (17y 4d) |