After defeating the trio on the Mayor's roof, they open a void that sends him to the Oogie Corridor. While navigating the maze of caverns, Jack finds the imprisoned Holiday Leaders and an elevator that leads to the Town Square. He finds Oogie at the end of the maze, in a casino-esque setting, and battles him. Upon his defeat, Oogie reveals that Jack had only defeated his shadow, and that the real him was already in Christmas Town. Jack collects the Easter Holiday Door after defeating him, leaving the Christmas door as the only one out of his possession, and returns to the plaza via a sewage line beneath the casino. After instructing the Mayor to free the other Holiday Leaders, Jack heads to the Hinterlands to restore the Holiday Doors and follow Oogie. Partway through this process, he confronts Oogie's two strongest monsters, the Fire King and the Ice King, and claims the Christmas Door from them. After restoring the seven trees, he heads to , where he finds that Oogie has already wreaked havoc. After fixing it, he heads to another part of the town, where the real Oogie is standing in Santa's sleigh and watching a rig that he has created to murder Santa Claus.
Oogie has on a few occasions demonstrated the ability to animate and control his shadow. This is most prominent in Oogies Revenge were he uses it to fight Jack. The first time he attacks Jack at city hall were the shadow itself doesn't attack Jack, but summons ghosts to throw exploding dice. The second time he has the shadow disguise as himself and ambush him at the end of the maze and this time they fight in a recreation of his gambling lord dungeon that he calls "The Oogie Casino". He deminstrates a new ability which is a vacume mouth which sucks up things, such as explosive dice that are placed everywhere. After this fight, the shadow appears to be destroyed. He uses the one in the movie to voice the shadow on the moon light night.
Unlike most other Disney villains, Oogie has little to no magical powers to call his own. This, however, doesn't make him an easy opponent. He traps his enemies in battles on twisted, game-like, battle grounds. With spinning razor wheels, exploding dice, gun-toting robots, playing card soldiers and many more deadly objects, Oogie Boogie can prove himself to be a dangerous foe. in all his video game apearences he places traps everywhere he goes. in the pumpkin king he fills the town with arm catapults and firebreathing gargoyles. in oogies revenge he places gargoyle cannons and even a giant metal fish skeleton as well as making a complete replica of his mansion's torture chamber under the city hall and countless more(it is implied that Dr. Finkelstein helps him with these). in kingdom hearts 2 he some how converts santas workshop in to a gambling board torture chamber like his own back at his mansion in mere minutes.
Start in the Town Square, fight the skeletons and ghosts; the more souls you collect, the more special weapons you can earn. With those weapons, you can destroy Oogie forever. As you travel through the square, you meet the towns people who help you out with advice.