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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Roger Federer | Masters Cup | 2002-11-11 | Tour Finals | 2019-11-11 | 6209d (17y 4d) |
| 2 |  Novak Djokovic | Masters Cup | 2008-11-09 | Tour Finals | 2023-11-13 | 5482d (15y 7d) |
| 3 |  Rafael Nadal | Masters Cup | 2006-11-13 | Tour Finals | 2020-11-16 | 5117d (14y 7d) |
| 4 |  Andre Agassi | ATP Tour World Championship | 1990-11-12 | Masters Cup | 2003-11-10 | 4746d (13y 1d) |
| 5 | Jimmy Connors | Masters | 1972-11-28 | Masters | 1985-01-08 | 4424d (12y 44d) |
| 6 | John McEnroe | Masters | 1979-01-10 | Masters | 1989-11-28 | 3975d (10y 325d) |
| 7 |  Boris Becker | Masters | 1986-01-14 | ATP World Championships | 1996-11-19 | 3962d (10y 312d) |
| 8 | Ivan Lendl | Masters | 1981-01-14 | ATP Tour World Championships | 1991-11-12 | 3954d (10y 304d) |
| 9 | Pete Sampras | ATP Tour World Championships | 1991-11-12 | Tennis Masters Cup | 2000-11-27 | 3303d (9y 18d) |
| 10 |  Guillermo Vilas | Masters | 1974-12-10 | Masters | 1983-01-18 | 2961d (8y 41d) |