| Tuesday • July 30, 2019 | |||
| Commonwealth Cosmos FC | 8 - 1 | Kembangan United FC | Bedok Stadium |
| Winchester Isla FC | 3 - 2 | Gymkhana FC | Toa Payoh Stadium |
| Thursday • August 1, 2019 | |||
| GDT Circuit FC | 0 - 1 | Bedok South Avenue SC | Jalan Besar Stadium |
| Geylang Serai FC | 5 - 1 | Bukit Timah Juniors | St Wilfrid Sports Complex |
Commonwealth Cosmos F, Winchester Isla FC, Bedok South Avenue SC and Geylang Serai FC advanced to the Semi-Finals.
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