| 07 May 23 | r05        | Geylang InternationalGeylang Inter | 1 - 2 | Home UnitedHome United |
| 12 May 23 | r05        | Hougang UnitedHougang Unite | 3 - 2 | Geylang InternationalGeylang Inter |
| 13 May 23 | r05        | DPMM FCDPMM FC | 3 - 3 | Home UnitedHome United |
| 14 May 23 | r05        | Tampines RoversTampines Rove | 3 - 0 | Tanjong Pagar UnitedTanjong Pagar |
| 20 May 23 | r05        | Tampines RoversTampines Rove | 1 - 0 | Young LionsYoung Lions |
| 20 May 23 | r05        | Balestier KhalsaBalestier Kha | 3 - 2 | DPMM FCDPMM FC |
| 21 May 23 | r05        | Home UnitedHome United | 3 - 2 | Albirex Niigata SAlbirex Niiga |
| 21 May 23 | r05        | Geylang InternationalGeylang Inter | 2 - 3 | Tanjong Pagar UnitedTanjong Pagar |
| 26 May 23 | r05        | Albirex Niigata SAlbirex Niiga | 6 - 2 | Balestier KhalsaBalestier Kha |
| 27 May 23 | r05        | Young LionsYoung Lions | 0 - 2 | Geylang InternationalGeylang Inter |