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| Rank | Player | Wins | Year |
|---|---|---|---|
| 1 |  Jim Courier | 28 | 1995 |
| 2 | James Blake | 26 | 2006 |
| 3 | Michael Chang | 26 | 1993 |
| 4 | James Blake | 25 | 2007 |
| 5 |  Wayne Ferreira | 24 | 1994 |
| 6 |  Damir Dzumhur | 24 | 2017 |
| 7 |  Paradorn Srichaphan | 22 | 2002 |
| 8 |  Ivo Karlovic | 22 | 2007 |
| 9 |  Magnus Norman | 20 | 2000 |
| 10 | Paradorn Srichaphan | 20 | 2003 |
| 11 | James Blake | 20 | 2005 |
| 12 | Sam Querrey | 20 | 2009 |
| 13 | Thomas Enqvist | 19 | 1995 |
| 14 |  Rainer Schuettler | 19 | 2001 |
| 15 |  Janko Tipsarevic | 19 | 2011 |
| 16 | Jim Courier | 18 | 1997 |
| 17 | Andre Agassi | 18 | 1998 |
| 18 |  Tim Henman | 18 | 1998 |
| 19 | Michael Chang | 18 | 2000 |
| 20 |  Dominik Hrbaty | 18 | 2004 |