Woodlands Wellington 
| 2000-03-10 | S.League | Sembawang | (A) | 0 | - 0 | D | |
| 2000-03-18 | S.League | Tanjong Pagar United | (H) | 1 | - 2 | L | |
| 2000-03-24 | S.League | Gombak United FC | (A) | 0 | - 1 | L | |
| 2000-03-30 | S.League | Tampines Rovers FC | (H) | 3 | - 1 | W | |
| 2000-04-07 | S.League | Jurong | (H) | 0 | - 1 | L | |
| 2000-04-15 | S.League | Hougang United FC | (A) | 1 | - 4 | L | |
| 2000-04-21 | S.League | Geylang International | (H) | 0 | - 3 | L | |
| 2000-04-27 | S.League | Warriors FC | (A) | 0 | - 1 | L | |
| 2000-05-04 | S.League | Balestier Khalsa FC | (H) | 2 | - 0 | W | |
| 2000-05-13 | S.League | Clementi | (H) | 3 | - 0 | W | |
| 2000-05-19 | S.League | Home United FC | (A) | 0 | - 0 | D | |
| 2000-06-08 | S.League | Sembawang | (H) | 1 | - 2 | L | |
| 2000-06-15 | S.League | Tanjong Pagar United | (A) | 2 | - 2 | D | |
| 2000-06-22 | S.League | Gombak United FC | (H) | 0 | - 1 | L | |
| 2000-06-29 | S.League | Tampines Rovers FC | (A) | 1 | - 3 | L | |
| 2000-07-08 | S.League | Jurong | (A) | 1 | - 1 | D | |
| 2000-07-14 | S.League | Hougang United FC | (H) | 2 | - 0 | W | |
| 2000-07-22 | S.League | Geylang International | (A) | 0 | - 2 | L | |
| 2000-07-28 | S.League | Warriors FC | (H) | 0 | - 3 | L | |
| 2000-08-05 | S.League | Balestier Khalsa FC | (A) | 0 | - 1 | L | |
| 2000-08-12 | S.League | Clementi | (A) | 2 | - 2 | D | |
| 2000-08-19 | S.League | Home United FC | (H) | 0 | - 1 | L |