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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Jimmy Connors | Los Angeles-2 | 1970-09-21 | US Open | 1992-08-31 | 8015d (21y 350d) |
| 2 |  Gael Monfils | Australian Open | 2005-01-17 | Indian Wells Masters | 2026-03-05 | 7717d (21y 52d) |
| 3 |  Bjorn Borg | Stockholm WCT | 1971-10-30 | Washington | 1992-07-13 | 7562d (20y 262d) |
| 4 |  Novak Djokovic | Cincinnati Masters | 2005-08-15 | Indian Wells Masters | 2026-03-08 | 7510d (20y 210d) |
| 5 | Andre Agassi | La Quinta | 1986-02-24 | US Open | 2006-08-28 | 7490d (20y 190d) |
| 6 |  Stan Wawrinka | Canada Masters | 2005-08-08 | Australian Open | 2026-01-19 | 7469d (20y 169d) |
| 7 | Roger Federer | Washington | 1999-08-16 | Australian Open | 2020-01-20 | 7462d (20y 162d) |
| 8 | Fabrice Santoro | Miami Masters | 1990-03-16 | Paris Masters | 2009-11-08 | 7177d (19y 242d) |
| 9 |  Feliciano Lopez | Miami Masters | 2002-03-18 | Winston-Salem | 2021-08-23 | 7098d (19y 163d) |
| 10 | Rafael Nadal | US Open | 2003-08-25 | Australian Open | 2023-01-16 | 7084d (19y 149d) |