| 11 Apr 23 | r04        | Young LionsYoung Lions | 2 - 2 | DPMM FCDPMM FC |
| 12 Apr 23 | r04        | Geylang InternationalGeylang Inter | 3 - 0 | Balestier KhalsaBalestier Kha |
| 15 Apr 23 | r04        | Albirex Niigata SAlbirex Niiga | 2 - 0 | DPMM FCDPMM FC |
| 15 Apr 23 | r04        | Young LionsYoung Lions | 1 - 1 | Home UnitedHome United |
| 16 Apr 23 | r04        | Tanjong Pagar UnitedTanjong Pagar | 2 - 4 | Balestier KhalsaBalestier Kha |
| 16 Apr 23 | r04        | Hougang UnitedHougang Unite | 1 - 1 | Tampines RoversTampines Rove |
| 20 Apr 23 | r04        | Tampines RoversTampines Rove | 2 - 0 | DPMM FCDPMM FC |
| 05 May 23 | r04        | Tampines RoversTampines Rove | 2 - 3 | Balestier KhalsaBalestier Kha |
| 06 May 23 | r04        | Hougang UnitedHougang Unite | 0 - 5 | Albirex Niigata SAlbirex Niiga |
| 07 May 23 | r04        | DPMM FCDPMM FC | 2 - 1 | Tanjong Pagar UnitedTanjong Pagar |