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| 1st(1st leg) | Tampines Rovers | - | Lion City Sailors | 3:3 (2:2) | ||
| 2nd (2nd leg) | Lion City Sailors | - | Tampines Rovers | 3:0 (1:0) | ||
| 1st(1st leg): 03/12/2023 10:00 | 2nd (2nd leg): 06/12/2023 11:45 | Winner: Lion City Sailors | ||||
| 1st(1st leg) | Hougang United | - | DPMM FC | 1:0 (0:0) | ||
| 2nd (2nd leg) | DPMM FC | - | Hougang United | 0:2 (0:1) | ||
| 1st(1st leg): 03/12/2023 10:00 | 2nd (2nd leg): 06/12/2023 11:45 | Winner: Hougang United | ||||
