| 25 Feb 23 | r01        | Tampines RoversTampines Rove | 1 - 1 | Geylang InternationalGeylang Inter |
| 03 Mar 23 | r01        | Tanjong Pagar UnitedTanjong Pagar | 0 - 2 | Tampines RoversTampines Rove |
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| 09 Mar 23 | r02        | Young LionsYoung Lions | 0 - 3 | Tampines RoversTampines Rove |
| 14 Mar 23 | r02        | Balestier KhalsaBalestier Kha | 1 - 3 | Tampines RoversTampines Rove |
| |
| 19 Mar 23 | r03        | Albirex Niigata SAlbirex Niiga | 0 - 1 | Tampines RoversTampines Rove |
| 31 Mar 23 | r03        | Tampines RoversTampines Rove | 4 - 3 | Home UnitedHome United |
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| 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 |
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| 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 |
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| 28 May 23 | r06        | DPMM FCDPMM FC | 0 - 1 | Tampines RoversTampines Rove |
| 07 Jun 23 | r06        | Home UnitedHome United | 1 - 1 | Tampines RoversTampines Rove |
| 10 Jun 23 | r06        | Tampines RoversTampines Rove | 2 - 0 | Hougang UnitedHougang Unite |
| |
| 27 Jun 23 | r07        | Tampines RoversTampines Rove | 1 - 1 | Albirex Niigata SAlbirex Niiga |
| |
| 02 Jul 23 | r08        | Geylang InternationalGeylang Inter | 1 - 1 | Tampines RoversTampines Rove |
| 06 Jul 23 | r08        | Hougang UnitedHougang Unite | 0 - 1 | Tampines RoversTampines Rove |
| 11 Jul 23 | r08        | Tampines RoversTampines Rove | 2 - 1 | Tanjong Pagar UnitedTanjong Pagar |
| |
| 15 Jul 23 | r09        | Young LionsYoung Lions | 2 - 3 | Tampines RoversTampines Rove |
| 22 Jul 23 | r09        | Tampines RoversTampines Rove | 2 - 3 | Geylang InternationalGeylang Inter |
| 28 Jul 23 | r09        | Albirex Niigata SAlbirex Niiga | 6 - 3 | Tampines RoversTampines Rove |
| |
| 04 Aug 23 | r10        | Tampines RoversTampines Rove | 2 - 5 | Home UnitedHome United |
| |
| 18 Aug 23 | r11        | Tampines RoversTampines Rove | 2 - 2 | DPMM FCDPMM FC |
| 15 Sep 23 | r11        | Balestier KhalsaBalestier Kha | 1 - 3 | Tampines RoversTampines Rove |