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| 06.10.2018 | ||||
| 14:00 | Cup Final | Albirex Niigata (S) | 4-1 | Brunei DPMM FC |
| 11:00 | Cup 3rd Place | Home United | 2-2/p.4-5 | Balestier Khalsa |
| 03.10.2018 | ||||
| 13:45 | Cup Semifinal | Balestier Khalsa | 2-2 | Brunei DPMM FC |
| 13:45 | Cup Semifinal | Home United | 0-1 | Albirex Niigata (S) |
| 26.09.2018 | ||||
| 13:45 | Cup Semifinal | Albirex Niigata (S) | 3-2 | Home United |
| 13:45 | Cup Semifinal | Brunei DPMM FC | 2-0 | Balestier Khalsa |
| 19.09.2018 | ||||
| 13:45 | Cup Quarterfinal | Tampines Rovers | 1-3 | Home United |
| 13:45 | Cup Quarterfinal | Warriors FC (SG) | 0-3 | Brunei DPMM FC |
| 01.09.2018 | ||||
| 12:00 | Cup Quarterfinal | Albirex Niigata (S) | 2-0 | Hougang United |
| 12:00 | Cup Quarterfinal | Balestier Khalsa | 1-0 | Geylang International |
| 29.08.2018 | ||||
| 13:45 | Cup Quarterfinal | Geylang International | 0-0 | Balestier Khalsa |
| 13:45 | Cup Quarterfinal | Hougang United | 0-1 | Albirex Niigata (S) |