For Brothers Together, we won’t have this scenario showing up. It’s possible it may appear in a different AU, but it’s a difficult type of scene to write and the setting and the emotions have to fit.
With Oscar and the younger Winchesters, bullies usually pick on easy targets, which is why Sam had such trouble in school. He’s a scrawny kid. Dean might be the type to get into fights, but in this scenario he’s not looking for trouble. He’s keeping his head down in order to keep Sam safe, and he’s a dangerous enough looking guy that no one wants to go after him first.
And I doubt that Oscar would ever come out of the motel again if he was involved in a fight.