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| H | Tampines Rovers | - | Geylang International | 2:0 (1:0) | ||
| R | Geylang International | - | Tampines Rovers | 1:2 (0:1) | ||
| H: 26.10.2019 11:30 | R: 30.10.2019 12:45 | Sieger: Tampines Rovers | ||||
| H | DPMM FC | - | Warriors FC | 1:0 (1:0) | ||
| R | Warriors FC | - | DPMM FC | 4:2 (2:2, 4:3, 5:4) i.E. | ||
| H: 26.10.2019 11:30 | R: 30.10.2019 12:45 | Sieger: Warriors FC | ||||
