Woodlands Wellington 
| 2009-02-26 | S.League | Tampines Rovers FC | (H) | 2 | - 2 | D | |
| 2009-03-03 | S.League | Courts Young Lions | (H) | 0 | - 0 | D | |
| 2009-03-08 | S.League | Brunei DPMM FC | (A) | 1 | - 2 | L | |
| 2009-03-12 | S.League | Albirex Niigata (S) FC | (A) | 0 | - 3 | L | |
| 2009-03-22 | S.League | Warriors FC | (A) | 3 | - 2 | W | |
| 2009-03-26 | S.League | Gombak United FC | (H) | 1 | - 1 | D | |
| 2009-03-30 | S.League | Home United FC | (A) | 0 | - 4 | L | |
| 2009-04-06 | S.League | Balestier Khalsa FC | (A) | 1 | - 0 | W | |
| 2009-04-16 | S.League | Geylang International | (H) | 0 | - 2 | L | |
| 2009-04-23 | S.League | Hougang United FC | (A) | 0 | - 1 | L | |
| 2009-05-08 | S.League | Courts Young Lions | (A) | 1 | - 1 | D | |
| 2009-05-18 | S.League | Tampines Rovers FC | (A) | 1 | - 4 | L | |
| 2009-05-21 | S.League | Brunei DPMM FC | (H) | 2 | - 1 | W | |
| 2009-05-29 | S.League | Super Reds | (H) | 1 | - 0 | W | |
| 2009-06-22 | S.League | Albirex Niigata (S) FC | (H) | 0 | - 1 | L | |
| 2009-06-30 | S.League | Warriors FC | (H) | 1 | - 4 | L | |
| 2009-07-04 | S.League | Gombak United FC | (A) | 2 | - 1 | W | |
| 2009-07-07 | S.League | Home United FC | (H) | 2 | - 1 | W | |
| 2009-07-12 | S.League | Balestier Khalsa FC | (H) | 2 | - 1 | W | |
| 2009-07-15 | S.League | Geylang International | (A) | 0 | - 4 | L | |
| 2009-07-20 | S.League | Super Reds | (A) | 0 | - 0 | D | |
| 2009-07-30 | S.League | Hougang United FC | (H) | 0 | - 0 | D | |
| 2009-08-08 | S.League | Brunei DPMM FC | (A) | 0 | - 2 | L | |
| 2009-08-22 | S.League | Courts Young Lions | (H) | 0 | - 0 | D | |
| 2009-08-27 | S.League | Warriors FC | (A) | 0 | - 1 | L | |
| 2009-09-08 | S.League | Tampines Rovers FC | (H) | 1 | - 0 | W | |
| 2009-09-14 | S.League | Albirex Niigata (S) FC | (A) | 0 | - 2 | L | |
| 2009-09-18 | S.League | Gombak United FC | (H) | 0 | - 2 | L | |
| 2009-09-25 | S.League | Home United FC | (A) | 1 | - 3 | L | |
| 2009-10-07 | S.League | Super Reds | (H) | 2 | - 5 | L | |
| 2009-10-15 | S.League | Balestier Khalsa FC | (A) | 1 | - 0 | W | |
| 2009-10-20 | S.League | Geylang International | (H) | 0 | - 1 | L | |
| 2009-11-06 | S.League | Hougang United FC | (A) | 1 | - 2 | L |