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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Roger Federer | Roland Garros | 2000-05-29 | Wimbledon | 2021-06-28 | 7700d (21y 35d) |
| 2 |  Novak Djokovic | Roland Garros | 2006-05-29 | Australian Open | 2026-01-24 | 7180d (19y 245d) |
| 3 |  Jimmy Connors | Wimbledon | 1972-06-26 | US Open | 1991-08-26 | 7000d (19y 65d) |
| 4 |  Gael Monfils | Roland Garros | 2006-05-29 | Australian Open | 2025-01-13 | 6804d (18y 234d) |
| 5 |  Rafael Nadal | Australian Open | 2005-01-17 | US Open | 2022-08-29 | 6433d (17y 228d) |
| 6 |  Marin Cilic | Australian Open | 2008-01-14 | Wimbledon | 2025-06-30 | 6377d (17y 172d) |
| 7 | Andre Agassi | Roland Garros | 1988-05-23 | US Open | 2005-08-29 | 6307d (17y 102d) |
| 8 | John McEnroe | Wimbledon | 1977-06-20 | US Open | 1992-08-31 | 5551d (15y 76d) |
| 9 |  Phil Dent | Australian Championships | 1968-01-19 | Australian Open | 1982-12-02 | 5431d (14y 321d) |
| 10 | Ivan Lendl | Roland Garros | 1979-05-28 | Australian Open | 1994-01-17 | 5348d (14y 238d) |