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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Roger Federer | Australian Open | 2000-01-17 | Wimbledon | 2021-06-28 | 7833d (21y 168d) |
| 2 | Stan Wawrinka | Roland Garros | 2005-05-23 | Australian Open | 2026-01-22 | 7549d (20y 249d) |
| 3 |  Novak Djokovic | Wimbledon | 2005-06-20 | Australian Open | 2026-01-22 | 7521d (20y 221d) |
| 4 |  Gael Monfils | Wimbledon | 2005-06-20 | Australian Open | 2025-01-13 | 7147d (19y 212d) |
| 5 |  Jimmy Connors | Roland Garros | 1972-05-22 | US Open | 1991-08-26 | 7035d (19y 100d) |
| 6 |  Rafael Nadal | Wimbledon | 2003-06-23 | US Open | 2022-08-29 | 7007d (19y 72d) |
| 7 | Feliciano Lopez | Wimbledon | 2002-06-24 | Australian Open | 2021-02-08 | 6804d (18y 234d) |
| 8 | Fabrice Santoro | US Open | 1990-08-27 | Australian Open | 2009-01-19 | 6720d (18y 150d) |
| 9 | Andre Agassi | Roland Garros | 1988-05-23 | US Open | 2006-08-28 | 6671d (18y 101d) |
| 10 |  Marin Cilic | Australian Open | 2008-01-14 | Australian Open | 2026-01-22 | 6583d (18y 13d) |