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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Novak Djokovic | Masters Cup | 2008-11-09 | Tour Finals | 2023-11-13 | 5482d (15y 7d) |
| 2 |  Andre Agassi | ATP Tour World Championship | 1990-11-12 | Masters Cup | 2003-11-10 | 4746d (13y 1d) |
| 3 |  Roger Federer | Masters Cup | 2003-11-10 | ATP Finals | 2015-11-15 | 4388d (12y 8d) |
| 4 |  Boris Becker | Masters | 1986-01-14 | ATP World Championships | 1996-11-19 | 3962d (10y 312d) |
| 5 | Pete Sampras | ATP Tour World Championships | 1991-11-12 | ATP Tour World Championship | 1999-11-22 | 2932d (8y 12d) |
| 6 | Ivan Lendl | Masters | 1981-01-14 | Masters | 1988-11-30 | 2877d (7y 322d) |
| 7 | John McEnroe | Masters | 1979-01-10 | Masters | 1985-01-08 | 2190d (6y 0d) |
| 8 |  Bjorn Borg | Masters | 1975-11-30 | Masters | 1981-01-14 | 1872d (5y 47d) |
| 9 |  Ilie Nastase | Masters | 1971-12-04 | Masters | 1975-11-30 | 1457d (3y 362d) |
| 10 |  Lleyton Hewitt | Masters Cup | 2001-11-12 | Masters Cup | 2004-11-15 | 1099d (3y 4d) |