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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 |  Jimmy Connors | US Open | 1971-09-01 | US Open | 1992-08-31 | 7670d (21y 5d) |
| 3 |  Novak Djokovic | Roland Garros | 2005-05-23 | Australian Open | 2026-01-19 | 7546d (20y 246d) |
| 4 | Stan Wawrinka | Roland Garros | 2005-05-23 | Australian Open | 2026-01-19 | 7546d (20y 246d) |
| 5 |  Gael Monfils | Australian Open | 2005-01-17 | Wimbledon | 2025-06-30 | 7469d (20y 169d) |
| 6 | Richard Gasquet | Roland Garros | 2005-05-23 | Roland Garros | 2025-05-26 | 7308d (20y 8d) |
| 7 |  Rafael Nadal | Wimbledon | 2003-06-23 | Australian Open | 2023-01-16 | 7147d (19y 212d) |
| 8 | Andre Agassi | Roland Garros | 1987-05-25 | US Open | 2006-08-28 | 7035d (19y 100d) |
| 9 | Fabrice Santoro | Roland Garros | 1990-05-28 | Wimbledon | 2009-06-22 | 6965d (19y 30d) |
| 10 | Feliciano Lopez | Roland Garros | 2002-05-27 | Australian Open | 2021-02-08 | 6832d (18y 262d) |