Singapore Cup Singapore Cup Singapore Cup

| Year_ | Champions | Runners_up | Score_in_the_final | _3rd_place | _4th_place |
|---|---|---|---|---|---|
| 1998 | Tanjong Pagar United | Singapore Armed Forces | 2–0 | Home United | Sembawang Rangers |
| 1999 | Singapore Armed Forces | Jurong FC | 3–1 | Home United | Balestier Central |
| 2000 | Home United | Singapore Armed Forces | 1–0 | Geylang United | Woodlands Wellington |
| 2001 | Home United | Geylang United | 8–0 | Singapore Armed Forces | Tanjong Pagar United |
| 2002 | Tampines Rovers | Jurong FC | 1–0 | Geylang United | Sengkang Marine |
| 2003 | Home United | Geylang United | 2–1 | Jurong FC , Woodlands Wellington | No 3rd-place playoff |
| 2004 | Tampines Rovers | Home United | 4–1 (aet) | Geylang United , Sinchi FC | No 3rd-place playoff |
| 2005 | Home United | Woodlands Wellington | 3–2 | Singapore Armed Forces , Tampines Rovers | No 3rd-place playoff |