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| 1st(1st leg) | Balestier Khalsa | - | Home United | 2:1 (1:0) | ||
| 2nd (2nd leg) | Home United | - | Balestier Khalsa | 2:2 (1:1) | ||
| 1st(1st leg): 27/06/2016 13:00 | 2nd (2nd leg): 30/06/2016 13:00 | Winner: Balestier Khalsa | ||||
| 1st(1st leg) | Albirex Niigata (S) | - | Geylang International | 2:0 (1:0) | ||
| 2nd (2nd leg) | Geylang International | - | Albirex Niigata (S) | 2:2 (2:0) | ||
| 1st(1st leg): 28/06/2016 13:00 | 2nd (2nd leg): 01/07/2016 13:00 | Winner: Albirex Niigata (S) | ||||
| 1st(1st leg) | Tampines Rovers | - | Global FC | 3:1 (1:1) | ||
| 2nd (2nd leg) | Global FC | - | Tampines Rovers | 1:2 | ||
| 1st(1st leg): 29/06/2016 13:00 | 2nd (2nd leg): 02/07/2016 13:00 | Winner: Tampines Rovers | ||||
| 1st(1st leg) | DPMM FC | - | Ceres FC | 0:3 (0:2) | ||
| 2nd (2nd leg) | Ceres FC | - | DPMM FC | 2:3 | ||
| 1st(1st leg): 30/06/2016 13:00 | 2nd (2nd leg): 03/07/2016 13:00 | Winner: Ceres FC | ||||
