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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Roger Federer | Roland Garros | 2001-05-28 | Wimbledon | 2021-06-28 | 7336d (20y 36d) |
| 2 |  Novak Djokovic | Roland Garros | 2006-05-29 | Australian Open | 2026-01-28 | 7184d (19y 249d) |
| 3 |  Jimmy Connors | Wimbledon | 1972-06-26 | US Open | 1991-08-26 | 7000d (19y 65d) |
| 4 | Andre Agassi | Roland Garros | 1988-05-23 | US Open | 2005-08-29 | 6307d (17y 102d) |
| 5 |  Rafael Nadal | Roland Garros | 2005-05-23 | Wimbledon | 2022-06-27 | 6244d (17y 39d) |
| 6 | John McEnroe | Wimbledon | 1977-06-20 | Wimbledon | 1992-06-22 | 5481d (15y 6d) |
| 7 |  Tommy Haas | Australian Open | 1999-01-18 | Roland Garros | 2013-05-27 | 5243d (14y 133d) |
| 8 |  Gael Monfils | Roland Garros | 2008-05-25 | Australian Open | 2022-01-17 | 4985d (13y 240d) |
| 9 |  Marin Cilic | US Open | 2009-08-31 | Roland Garros | 2022-05-23 | 4648d (12y 268d) |
| 10 | Boris Becker | Australian Open | 1984-11-26 | Wimbledon | 1997-06-23 | 4592d (12y 212d) |
| 11 | Goran Ivanisevic | Australian Open | 1989-01-16 | Wimbledon | 2001-06-25 | 4543d (12y 163d) |
| 12 | Ivan Lendl | US Open | 1980-08-26 | US Open | 1992-08-31 | 4388d (12y 8d) |
| 13 | Pete Sampras | US Open | 1990-08-27 | US Open | 2002-08-26 | 4382d (12y 2d) |
| 14 |  Phil Dent | Australian Championships | 1968-01-19 | Australian Open | 1979-12-24 | 4357d (11y 342d) |
| 15 |  Jonas Bjorkman | US Open | 1994-08-29 | Wimbledon | 2006-06-26 | 4319d (11y 304d) |
| 16 | Stefan Edberg | Australian Open | 1984-11-26 | US Open | 1996-08-26 | 4291d (11y 276d) |
| 17 |  Tom Okker | Wimbledon | 1968-06-24 | Wimbledon | 1979-06-25 | 4018d (11y 3d) |
| 18 |  Wayne Ferreira | Australian Open | 1992-01-13 | Australian Open | 2003-01-13 | 4018d (11y 3d) |
| 19 |  Guillermo Vilas | Roland Garros | 1975-06-04 | Roland Garros | 1986-05-26 | 4009d (10y 359d) |
| 20 | Roscoe Tanner | US Open | 1972-08-30 | Wimbledon | 1983-06-20 | 3946d (10y 296d) |