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| Rank | Player | Reaches | Tournament |
|---|---|---|---|
| 1 |  Rafael Nadal | 12 | Monte Carlo Masters |
| 2 | Rafael Nadal | 12 | Rome Masters |
| 3 |  Novak Djokovic | 12 | Rome Masters |
| 4 |  Roger Federer | 9 | Indian Wells Masters |
| 5 | Novak Djokovic | 9 | Paris Masters |
| 6 |  Andre Agassi | 8 | Miami Masters |
| 7 | Roger Federer | 8 | Cincinnati Masters |
| 8 | Rafael Nadal | 8 | Madrid Masters |
| 9 | Novak Djokovic | 8 | Miami Masters |
| 10 | Novak Djokovic | 8 | Cincinnati Masters |
| 11 | Roger Federer | 6 | Canada Masters |
| 12 | Novak Djokovic | 6 | Indian Wells Masters |
| 13 | Pete Sampras | 5 | Cincinnati Masters |
| 14 | Roger Federer | 5 | Miami Masters |
| 15 | Roger Federer | 5 | Hamburg Masters |
| 16 | Rafael Nadal | 5 | Miami Masters |
| 17 | Rafael Nadal | 5 | Canada Masters |
| 18 | Roger Federer | 5 | Madrid Masters |
| 19 | Rafael Nadal | 5 | Indian Wells Masters |
| 20 | Novak Djokovic | 5 | Canada Masters |