| 28 May 23 | r06        | DPMM FCDPMM FC | 0 - 1 | Tampines RoversTampines Rove |
| 28 May 23 | r06        | Tanjong Pagar UnitedTanjong Pagar | 1 - 3 | Hougang UnitedHougang Unite |
| 01 Jun 23 | r06        | Balestier KhalsaBalestier Kha | 4 - 5 | Home UnitedHome United |
| 03 Jun 23 | r06        | Hougang UnitedHougang Unite | 3 - 0 | Young LionsYoung Lions |
| 06 Jun 23 | r06        | Young LionsYoung Lions | 3 - 4 | Tanjong Pagar UnitedTanjong Pagar |
| 06 Jun 23 | r06        | Albirex Niigata SAlbirex Niiga | 3 - 0 | Geylang InternationalGeylang Inter |
| 07 Jun 23 | r06        | Home UnitedHome United | 1 - 1 | Tampines RoversTampines Rove |
| 07 Jun 23 | r06        | DPMM FCDPMM FC | 2 - 3 | Hougang UnitedHougang Unite |
| 10 Jun 23 | r06        | Home UnitedHome United | 4 - 1 | Young LionsYoung Lions |
| 10 Jun 23 | r06        | Tampines RoversTampines Rove | 2 - 0 | Hougang UnitedHougang Unite |