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