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| 30.03.2025 | ||||
| 14:30 | Cup Group B | BG Pathum United | 1-1 | Lion City Sailors |
| 29.03.2025 | ||||
| 13:30 | Cup Group B | Balestier Khalsa | 3-0 | Tanjong Pagar Utd |
| 13:30 | Cup Group A | Hougang United | 1-5 | Tampines Rovers |
| 28.03.2025 | ||||
| 13:30 | Cup Group A | Young Lions | 7-1 | Albirex Niigata (S) |
| 27.03.2025 | ||||
| 13:30 | Cup Group B | Geylang International | 1-3 | Lion City Sailors |
| 16.03.2025 | ||||
| 13:30 | Cup Group B | Lion City Sailors | 4-1 | Balestier Khalsa |
| 13:30 | Cup Group A | Tampines Rovers | 4-1 | Young Lions |
| 15.03.2025 | ||||
| 13:30 | Cup Group A | Brunei DPMM FC | 1-5 | Hougang United |
| 13:30 | Cup Group B | Tanjong Pagar Utd | 1-0 | Geylang International |
| 03.03.2025 | ||||
| 13:30 | Cup Group A | Brunei DPMM FC | 3-1 | Albirex Niigata (S) |
| 02.03.2025 | ||||
| 13:30 | Cup Group B | Balestier Khalsa | 1-2 | BG Pathum United |
| 01.03.2025 | ||||
| 11:00 | Cup Group A | Hougang United | 0-3 | Young Lions |
| 22.04.2025 | |||||
| 13:45 | Cup Semifinal | Lion City Sailors | - | Brunei DPMM FC | |
| 13:45 | Cup Semifinal | Tampines Rovers | - | BG Pathum United | |
| 06.05.2025 | |||||
| 13:45 | Cup Semifinal | BG Pathum United | - | Tampines Rovers | |
| 13:45 | Cup Semifinal | Brunei DPMM FC | - | Lion City Sailors | |
| 31.05.2025 | |||||
| 12:00 | Cup 3rd Place | Loser SF 1 | - | Loser SF 2 | |
| 01.06.2025 | |||||
| 12:00 | Cup Final | Winner SF 1 | - | Winner SF 2 | |