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| 1st(1st leg) | Tampines Rovers | - | Tanjong Pagar United | 4:2 (1:1) | ||
| 2nd (2nd leg) | Tanjong Pagar United | - | Tampines Rovers | 1:4 (0:2) | ||
| 1st(1st leg): 27/06/2014 12:30 | 2nd (2nd leg): 01/07/2014 13:00 | Winner: Tampines Rovers | ||||
| 1st(1st leg) | Balestier Khalsa | - | Geylang International | 2:1 (0:1) | ||
| 2nd (2nd leg) | Geylang International | - | Balestier Khalsa | 3:4 pso | ||
| 1st(1st leg): 28/06/2014 12:30 | 2nd (2nd leg): 02/07/2014 13:00 | Winner: Balestier Khalsa | ||||
| 1st(1st leg) | Albirex Niigata (S) | - | DPMM FC | 3:4 (1:3) | ||
| 2nd (2nd leg) | DPMM FC | - | Albirex Niigata (S) | 2:1 (2:0) | ||
| 1st(1st leg): 29/06/2014 13:00 | 2nd (2nd leg): 04/07/2014 13:00 | Winner: DPMM FC | ||||
| 1st(1st leg) | Home United | - | Loyola Meralco Sparks | 2:0 (0:0) | ||
| 2nd (2nd leg) | Loyola Meralco Sparks | - | Home United | 1:2 (0:2) | ||
| 1st(1st leg): 30/06/2014 13:00 | 2nd (2nd leg): 03/07/2014 13:00 | Winner: Home United | ||||
