Woodlands Wellington 
| 1999-03-31 | S.League | Home United FC | (A) | 1 | - 4 | L | |
| 1999-04-07 | S.League | Gombak United FC | (H) | 1 | - 2 | L | |
| 1999-04-17 | S.League | Warriors FC | (A) | 0 | - 7 | L | |
| 1999-04-21 | S.League | Jurong | (H) | 1 | - 1 | D | |
| 1999-04-30 | S.League | Clementi | (A) | 3 | - 4 | L | |
| 1999-05-07 | S.League | Tanjong Pagar United | (H) | 1 | - 2 | L | |
| 1999-05-15 | S.League | Tampines Rovers FC | (A) | 2 | - 0 | W | |
| 1999-05-21 | S.League | Sembawang | (H) | 1 | - 1 | D | |
| 1999-05-27 | S.League | Balestier Khalsa FC | (A) | 0 | - 1 | L | |
| 1999-06-05 | S.League | Geylang International | (H) | 3 | - 2 | W | |
| 1999-06-12 | S.League | Hougang United FC | (A) | 3 | - 1 | W | |
| 1999-06-19 | S.League | Home United FC | (H) | 1 | - 3 | L | |
| 1999-06-25 | S.League | Gombak United FC | (A) | 2 | - 2 | D | |
| 1999-08-18 | S.League | Warriors FC | (H) | 1 | - 3 | L | |
| 1999-08-28 | S.League | Jurong | (A) | 0 | - 4 | L | |
| 1999-09-01 | S.League | Clementi | (H) | 1 | - 1 | D | |
| 1999-09-11 | S.League | Tanjong Pagar United | (A) | 0 | - 1 | L | |
| 1999-09-17 | S.League | Tampines Rovers FC | (H) | 3 | - 0 | W | |
| 1999-09-25 | S.League | Sembawang | (A) | 1 | - 3 | L | |
| 1999-09-29 | S.League | Balestier Khalsa FC | (H) | 1 | - 0 | W | |
| 1999-10-08 | S.League | Geylang International | (A) | 1 | - 2 | L | |
| 1999-10-16 | S.League | Hougang United FC | (H) | 3 | - 0 | W |