Teams
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Albirex Niigata Singapore F.C. - Balestier Khalsa FC
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Dalian Shide Siwu FC - Geylang United FC
- Gombak United FC
- Home United FC
- Sengkang Punggol FC
- Singapore Armed Forces FC (SAFFC)
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Super Reds FC - Tampines Rovers FC
- Woodlands Wellington FC
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Young Lions
Round one
The draw for the first knockout round was held on Tuesday, 13 May 2008 in Singapore. The first round matches began on 30 May. The winners advanced to the quarter-final stage. Teams who had finished in the top 4 positions of the 2007 S.League received a bye and did not participate in the round one knockout competition. The four byes were Singapore Armed Force FC, Home United, Tampines Rovers and Gombak United respectively.
| Woodlands Wellington | 3 – 3 (A.E.T) (4 – 5 pens) |  Young Lions |
|---|---|---|
Park Tae Won (Pen.)  44', 90'Fadzuhasny Juraimi 107' | Report | K Sivaseshan 90+1' Zulfadli Zainal Abidin 90+3'Obadin Aikhena 111' |
 Super Reds | 3 – 0 | Sengkang Punggol |
|---|---|---|
| Sin Hyun Ho (Pen.) 3' Oh Ddog Yi 9'Seo Su Jong 43' | Report |
| Geylang United | 1 – 2 | Balestier Khalsa |
|---|---|---|
| Miroslav Latiak 30' | Report | Mba Vitus Onyekachi 22', Faizal Amir 63' |
Knockout Bracket - Starting from Quarter-Finals
| Quarter-final | Semi-final | Final | ||||||||||||
| Home United | 1, 0 (1) | |||||||||||||
| Gombak United | 1, 1 (2) | |||||||||||||
| Gombak United | 4, 1 (5) | |||||||||||||
| Young Lions | 1, 1 (2) | |||||||||||||
| Young Lions | 0, 3 (3) | |||||||||||||
| Tampines Rovers | 1, 2 (3) | |||||||||||||
| Gombak United | 2 | |||||||||||||
| Super Reds | 1 | |||||||||||||
| SAFFC | 0, 1 (1) | |||||||||||||
| Balestier Khalsa | 3, 2 (5) | |||||||||||||
| Balestier Khalsa | 0, 0 (0) | |||||||||||||
| Super Reds | 1, 0 (1) | |||||||||||||
| Super Reds | 3, 3 (6) | |||||||||||||
 Albirex Niigata FC (S) | 0, 1 (1) | |||||||||||||
