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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Andre Agassi | Masters | 1988-11-30 | Masters Cup | 2005-11-14 | 6193d (16y 353d) |
| 2 | John McEnroe | Masters | 1979-01-10 | Masters | 1989-11-28 | 3975d (10y 325d) |
| 3 |  Boris Becker | Masters | 1986-01-14 | ATP World Championships | 1996-11-19 | 3962d (10y 312d) |
| 4 | Ivan Lendl | Masters | 1981-01-14 | ATP Tour World Championships | 1991-11-12 | 3954d (10y 304d) |
| 5 | Jimmy Connors | Masters | 1978-01-04 | Masters | 1987-12-02 | 3619d (9y 334d) |
| 6 |  Stefan Edberg | Masters | 1986-01-14 | ATP Tour World Championships | 1994-11-15 | 3227d (8y 307d) |
| 7 | Arthur Ashe | Masters | 1970-12-07 | Masters | 1979-01-10 | 2956d (8y 36d) |
| 8 |  Andres Gomez | Masters | 1983-01-18 | ATP Tour World Championship | 1990-11-12 | 2855d (7y 300d) |
| 9 |  Guillermo Vilas | Masters | 1975-11-30 | Masters | 1983-01-18 | 2606d (7y 51d) |
| 10 | Michael Chang | Masters | 1989-11-28 | ATP World Championships | 1996-11-19 | 2548d (6y 358d) |