Zechariah 12 predicts that Jerusalem would become a "cup of reeling" and a "burdensome stone" to all the nations that gather against it. Historically, the Roman Empire was indeed wounded by its struggle to conquer Judea, but the ultimate "reeling" happened within the city itself.
During the siege of AD 70, Jerusalem was gripped by a spirit of madness. Rival factions murdered each other within the temple courts while the enemy was at the gates. They were "intoxicated" by their own rebellion. This localized judgment fulfilled Zechariah’s prophecy, clearing the way for the true, peaceful Jerusalem of the New Covenant to be fully established.