| 02 Jul 23 | r08        | Hougang UnitedHougang Unite | 1 - 3 | Balestier KhalsaBalestier Kha |
| 02 Jul 23 | r08        | Geylang InternationalGeylang Inter | 1 - 1 | Tampines RoversTampines Rove |
| 06 Jul 23 | r08        | Hougang UnitedHougang Unite | 0 - 1 | Tampines RoversTampines Rove |
| 06 Jul 23 | r08        | Tanjong Pagar UnitedTanjong Pagar | 2 - 3 | Balestier KhalsaBalestier Kha |
| 07 Jul 23 | r08        | Young LionsYoung Lions | 0 - 4 | Home UnitedHome United |
| 08 Jul 23 | r08        | DPMM FCDPMM FC | 1 - 1 | Albirex Niigata SAlbirex Niiga |
| 11 Jul 23 | r08        | Home UnitedHome United | 1 - 3 | DPMM FCDPMM FC |
| 11 Jul 23 | r08        | Tampines RoversTampines Rove | 2 - 1 | Tanjong Pagar UnitedTanjong Pagar |
| 12 Jul 23 | r08        | Geylang InternationalGeylang Inter | 0 - 2 | Hougang UnitedHougang Unite |
| 12 Jul 23 | r08        | Balestier KhalsaBalestier Kha | 4 - 2 | Young LionsYoung Lions |