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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Jimmy Connors | Columbus | 1971-07-26 | San Francisco | 1993-02-01 | 7861d (21y 196d) |
| 2 |  Rafael Nadal | Umag | 2003-07-21 | Bastad | 2024-07-15 | 7665d (21y 0d) |
| 3 |  Roger Federer | Vienna | 1999-10-11 | Australian Open | 2020-01-20 | 7406d (20y 106d) |
| 4 |  Novak Djokovic | Zagreb | 2006-01-30 | Australian Open | 2026-01-28 | 7303d (20y 3d) |
| 5 |  Marin Cilic | Gstaad | 2006-07-10 | Dallas | 2026-02-13 | 7158d (19y 223d) |
| 6 |  Gael Monfils | Sopot | 2005-08-01 | Auckland | 2025-01-06 | 7098d (19y 163d) |
| 7 | Stan Wawrinka | Gstaad | 2005-07-04 | Stockholm | 2024-10-14 | 7042d (19y 107d) |
| 8 | Richard Gasquet | Buenos Aires | 2004-02-16 | Auckland | 2023-01-09 | 6902d (18y 332d) |
| 9 | Fabrice Santoro | Toulouse | 1990-10-01 | Newport | 2009-07-06 | 6853d (18y 283d) |
| 10 | Andre Agassi | Seoul | 1987-04-20 | US Open | 2005-08-29 | 6706d (18y 136d) |