| Match Number | Cup Round 1 | ||||
| 1 | Gaulois SC | vs | TGA Legends | ||
| 2 | DHL Gaelic Lions | vs | Dragon Warriors FC | ||
| 3 | BLAS | vs | Hotspurs FC | ||
| 4 | St Andrews FC | vs | Casuals | ||
| 5 | Exiles FC | vs | Brazilian Football Association | ||
| 6 | Singapore Cricket Club Tigers | vs | Unity Sports Club | ||
| 7 | Sekret Safari FC | vs | British Club Lions | ||
| 8 | Big Poppas FC | vs | Fighting Cocks FC | ||
| 9 | CBD Wanderers | vs | Hibernians Wanderers | ||
| 10 | Tanglin Trust FC | vs | German All Stars Social | ||
| 11 | Saturday Night Live FC | vs | Hilderinc FC | ||
| 12 | Hibernians United | vs | Mariners FC | ||
| 13 | 1 Tanah Merah Legends | vs | TGA Strollers | ||
| 14 | Vikings Vets | vs | International Lions | ||