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| Rank | Player | Wins | Year |
|---|---|---|---|
| 1 |  John Frawley | 9 | 1988 |
| 2 |  Sebastien Grosjean | 8 | 2000 |
| 3 | Bernard Tomic | 8 | 2015 |
| 4 |  Denis Shapovalov | 8 | 2019 |
| 5 |  Tommy Paul | 8 | 2023 |
| 6 | Ben Shelton | 8 | 2024 |
| 7 | Dan Goldie | 8 | 1988 |
| 8 | Wally Masur | 8 | 1992 |
| 9 | Clark Graebner | 7 | 1968 |
| 10 | Jim Grabb | 7 | 1994 |
| 11 | Patrick Rafter | 7 | 1995 |
| 12 | Andy Roddick | 7 | 2004 |
| 13 |  Nicolas Kiefer | 7 | 1998 |
| 14 | Todd Martin | 7 | 1998 |
| 15 | Jan-Michael Gambill | 7 | 1998 |
| 16 | Fabrice Santoro | 7 | 1999 |
| 17 |  Yevgeny Kafelnikov | 7 | 2000 |
| 18 |  Marcelo Rios | 7 | 2002 |
| 19 | Fernando Gonzalez | 7 | 2002 |
| 20 |  David Nalbandian | 7 | 2007 |