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| H | Balestier Khalsa | - | Home United | 2:1 (1:0) | ||
| R | Home United | - | Balestier Khalsa | 2:2 (1:1) | ||
| H: 27.06.2016 14:00 | R: 30.06.2016 14:00 | Sieger: Balestier Khalsa | ||||
| H | Albirex Niigata (S) | - | Geylang International | 2:0 (1:0) | ||
| R | Geylang International | - | Albirex Niigata (S) | 2:2 (2:0) | ||
| H: 28.06.2016 14:00 | R: 01.07.2016 14:00 | Sieger: Albirex Niigata (S) | ||||
| H | Tampines Rovers | - | Global FC | 3:1 (1:1) | ||
| R | Global FC | - | Tampines Rovers | 1:2 | ||
| H: 29.06.2016 14:00 | R: 02.07.2016 14:00 | Sieger: Tampines Rovers | ||||
| H | DPMM FC | - | Ceres FC | 0:3 (0:2) | ||
| R | Ceres FC | - | DPMM FC | 2:3 | ||
| H: 30.06.2016 14:00 | R: 03.07.2016 14:00 | Sieger: Ceres FC | ||||
