Source: S-League[usurped] On 12 July 2012, Woodlands was drawn into Group D of the Starhub League Cup together with Tampines Rovers and Gombak United.

The 2012 edition of the Cup, which will run from July 26 to August 11, 2012, will be played in a new format that will see four groups of three teams each battle it out for a place in the semi-finals.

[23] Woodlands loses their first Starhub League Cup preliminary round match to Tampines Rovers with a 3-1 defeat before drawing their second game with Gombak United and finished bottom of Group D, leaving their fate of advancing to the quarter-finals to be decided by the match between Gombak United and Tampines Rovers on 2 August.

Gombak United and Tampines Rovers drew their League Cup preliminary round match and both teams advance to the quarter-finals while Woodlands, as the bottom placed team of Group D table, advance to the semi-finals of the newly created Plate Competition to face Balestier Khalsa on 6 August 2012.

Woodlands Wellington crashed out of the League Cup Plate Competition on 6 August 2012 after losing 1-0 to Balestier Khalsa in the semi-final, conceding a 67th goal to former Ram Zulkiffli Hassim.