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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Feliciano Lopez | Long Island | 2002-08-19 | Winston-Salem | 2021-08-23 | 6944d (19y 9d) |
| 2 |  Yen-Hsun Lu | Indianapolis | 2004-07-19 | Great Ocean Road Open | 2021-02-01 | 6041d (16y 201d) |
| 3 |  Andy Murray | Indianapolis | 2005-07-18 | Winston-Salem | 2021-08-23 | 5880d (16y 40d) |
| 4 |  Andreas Seppi | New Haven | 2005-08-22 | Winston-Salem | 2021-08-23 | 5845d (16y 5d) |
| 5 |  Julien Benneteau | Indianapolis | 2003-07-21 | Winston-Salem | 2018-08-20 | 5509d (15y 34d) |
| 6 | Gilles Simon | New Haven | 2006-08-21 | Winston-Salem | 2021-08-23 | 5481d (15y 6d) |
| 7 |  Sam Querrey | Indianapolis | 2006-07-17 | Great Ocean Road Open | 2021-02-01 | 5313d (14y 203d) |
| 8 |  Janko Tipsarevic | Indianapolis | 2003-07-21 | Winston-Salem | 2017-08-21 | 5145d (14y 35d) |
| 9 | Fabio Fognini | New Haven | 2008-08-17 | Winston-Salem | 2022-08-22 | 5118d (14y 8d) |
| 10 | Paul-Henri Mathieu | Long Island | 2002-08-19 | Winston-Salem | 2016-08-22 | 5117d (14y 7d) |