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| 1st(1st leg) | Home United | - | Tampines Rovers | 1:2 (0:1) | ||
| 2nd (2nd leg) | Tampines Rovers | - | Home United | 1:3 (1:2) | ||
| 1st(1st leg): 27/07/2018 12:45 | 2nd (2nd leg): 19/09/2018 12:45 | Winner: Home United | ||||
| 1st(1st leg) | DPMM FC | - | Warriors FC | 2:2 (0:2) | ||
| 2nd (2nd leg) | Warriors FC | - | DPMM FC | 0:3 (0:2) | ||
| 1st(1st leg): 23/08/2018 12:45 | 2nd (2nd leg): 19/09/2018 12:45 | Winner: DPMM FC | ||||
| 1st(1st leg) | Geylang International | - | Balestier Khalsa | 0:0 (0:0) | ||
| 2nd (2nd leg) | Balestier Khalsa | - | Geylang International | 1:0 (0:0) | ||
| 1st(1st leg): 29/08/2018 12:45 | 2nd (2nd leg): 01/09/2018 10:30 | Winner: Balestier Khalsa | ||||
| 1st(1st leg) | Hougang United | - | Albirex Niigata (S) | 0:1 (0:0) | ||
| 2nd (2nd leg) | Albirex Niigata (S) | - | Hougang United | 2:0 (1:0) | ||
| 1st(1st leg): 29/08/2018 12:45 | 2nd (2nd leg): 01/09/2018 10:30 | Winner: Albirex Niigata (S) | ||||
