2009 ATP World Tour Best 5 Matches by ATPWorldTour.com Best 5 Matches by ATPWorldTour.com

| _Event | Round | Surface | Winner | Opponent | Result_ |
|---|---|---|---|---|---|
| 1. | Wimbledon | Final | Grass | Roger Federer | Andy Roddick |
| 2. | Madrid | Semifinal | Clay | Rafael Nadal | Novak Djokovic |
| 3. | Australian Open | Semifinal | Hard | Rafael Nadal | Fernando Verdasco |
| 4. | US Open | 2nd Round | Hard | Taylor Dent | Iván Navarro |
| 5. | Tour Finals | Semifinal | Hard (i) | Nikolay Davydenko | Roger Federer |