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| 1st(1st leg) | Tampines Rovers | - | Geylang International | 2:0 (1:0) | ||
| 2nd (2nd leg) | Geylang International | - | Tampines Rovers | 1:2 (0:1) | ||
| 1st(1st leg): 26/10/2019 10:30 | 2nd (2nd leg): 30/10/2019 11:45 | Winner: Tampines Rovers | ||||
| 1st(1st leg) | DPMM FC | - | Warriors FC | 1:0 (1:0) | ||
| 2nd (2nd leg) | Warriors FC | - | DPMM FC | 4:2 (2:2, 4:3, 5:4) pso | ||
| 1st(1st leg): 26/10/2019 10:30 | 2nd (2nd leg): 30/10/2019 11:45 | Winner: Warriors FC | ||||
