Mentions légales
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| 19.06.2009 | ||||
| 13:45 | LC Final | Brunei DPMM FC | 1-1/p.4-3 | Singapore Armed Forces |
| 11:00 | LC 3rd Place | Woodlands Wellington | 2-2/p.1-4 | Home United |
| 16.06.2009 | ||||
| 13:45 | LC Semifinal | Home United | 0-2 | Singapore Armed Forces |
| 15.06.2009 | ||||
| 13:45 | LC Semifinal | Brunei DPMM FC | 2-1 | Woodlands Wellington |
| 13.06.2009 | ||||
| 13:45 | LC Quarterfinal | Tampines Rovers | 1-1/p.3-4 | Singapore Armed Forces |
| 12.06.2009 | ||||
| 13:45 | LC Quarterfinal | Brunei DPMM FC | 5-3 | Geylang United |
| 11.06.2009 | ||||
| 13:45 | LC Quarterfinal | Home United | 3-2 | Gombak United |
| 10.06.2009 | ||||
| 13:45 | LC Quarterfinal | Super Reds FC | 0-0/p.3-4 | Woodlands Wellington |
| 08.06.2009 | ||||
| 13:45 | LC Group A | Albirex Niigata (S) | 0-2 | Singapore Armed Forces |
| 13:45 | LC Group B | Young Lions | 1-0 | Tampines Rovers |
| 07.06.2009 | ||||
| 13:45 | LC Group C | Balestier Khalsa | 1-1 | Super Reds FC |
| 13:45 | LC Group D | Woodlands Wellington | 1-2 | Home United |