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| Rank | Player | Reaches | Tournament |
|---|---|---|---|
| 1 |  Roger Federer | 9 | Indian Wells Masters |
| 2 |  Novak Djokovic | 9 | Paris Masters |
| 3 |  Andre Agassi | 8 | Miami Masters |
| 4 | Roger Federer | 8 | Cincinnati Masters |
| 5 | Novak Djokovic | 8 | Miami Masters |
| 6 | Novak Djokovic | 8 | Cincinnati Masters |
| 7 | Roger Federer | 6 | Canada Masters |
| 8 | Novak Djokovic | 6 | Indian Wells Masters |
| 9 | Pete Sampras | 5 | Cincinnati Masters |
| 10 | Roger Federer | 5 | Miami Masters |