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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 |  Roger Federer | Vienna | 1999-10-11 | Australian Open | 2020-01-20 | 7406d (20y 106d) |
| 3 |  Novak Djokovic | Metz | 2006-10-02 | Australian Open | 2026-01-28 | 7058d (19y 123d) |
| 4 |  Gael Monfils | Metz | 2005-10-03 | Auckland | 2025-01-06 | 7035d (19y 100d) |
| 5 | Stan Wawrinka | Auckland | 2006-01-09 | Stockholm | 2024-10-14 | 6853d (18y 283d) |
| 6 | Andre Agassi | Seoul | 1987-04-20 | US Open | 2005-08-29 | 6706d (18y 136d) |
| 7 | Richard Gasquet | Metz | 2004-10-11 | Auckland | 2023-01-09 | 6664d (18y 94d) |
| 8 |  Rafael Nadal | Auckland | 2004-01-12 | Indian Wells Masters | 2022-03-07 | 6629d (18y 59d) |
| 9 |  Marin Cilic | Chennai | 2007-12-31 | Dallas | 2026-02-13 | 6619d (18y 49d) |
| 10 | Fabrice Santoro | Toulouse | 1990-10-01 | Moscow | 2008-10-06 | 6580d (18y 10d) |