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To help interpret this question, I have posted some of the surrounding verses to help a bit:

Zechariah 14:3-9: "Then the LORD will go forth and fight against those nations, as when He fights on a day of battle. 4In that day His feet will stand on the Mount of Olives, which is in front of Jerusalem on the east; and the Mount of Olives will be split in its middle from east to west by a very large valley, so that half of the mountain will move toward the north and the other half toward the south. 5You will flee by the valley of My mountains, for the valley of the mountains will reach to Azel; yes, you will flee just as you fled before the earthquake in the days of Uzziah king of Judah. Then the LORD, my God, will come, and all the holy ones with Him!

6In that day there will be no light; the luminaries will dwindle. 7For it will be a unique day which is known to the LORD, neither day nor night, but it will come about that at evening time there will be light. 8And in that day living waters will flow out of Jerusalem, half of them toward the eastern sea and the other half toward the western sea; it will be in summer as well as in winter. 9And the LORD will be king over all the earth; in that day the LORD will be the only one, and His name the only one."

What event is this describing, and when will "the Lord's feet stand on the Mount of Olives"?

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Zech 14:4 -In that day His feet will stand on the Mount of Olives, which is in front of Jerusalem on the east; and the Mount of Olives will be split in its middle from east to west by a very large valley, so that half of the mountain will move toward the north and the other half toward the south.

This is a very contentions verse for which a huge range of interpretations have been proposed. However, one thing is clear - it has never yet been fulfilled simply because we have never seen, "the Mount of Olives will be split in its middle from east to west by a very large valley"

The Cambridge commentary says:

4. the mount of Olives Comp. Acts 1:12. “The mount of Olives is the central eminence of a line of hills, of rather more than a mile in length, overhanging the city, from which it is separated only by the narrow bed of the valley of the Brook of Cedron. It rises 187 feet above mount Zion, 295 above mount Moriah, 443 above Gethsemane, and lies between the city and the wilderness toward the Dead Sea.” Pusey.

a very great valley The cleft in the mountain which is to form this valley will run E. and W., and will be caused by the two parts of the divided mountain moving N. and S.

When this will be fulfilled is another question entirely. Ellicott observes this:

14:1-7 The Lord Jesus often stood upon the Mount of Olives when on earth. He ascended from thence to heaven, and then desolations and distresses came upon the Jewish nation. Such is the view taken of this figuratively; but many consider it as a notice of events yet unfulfilled, and that it relates to troubles of which we cannot now form a full idea. Every believer, being related to God as his God, may triumph in the expectation of Christ's coming in power, and speak of it with pleasure. During a long season, the state of the church would be deformed by sin; there would be a mixture of truth and error, of happiness and misery. Such is the experience of God's people, a mingled state of grace and corruption. But, when the season is at the worst, and most unpromising, the Lord will turn darkness into light; deliverance comes when God's people have done looking for it.

What we can say:

Zech 14:1, 2 appears to be referring to the (then still future) time when Rome would devastate Jerusalem.

However, V3 and onwards appears to be prophesying about another time when God would destroy the nations that gather to fight against Jerusalem. Whatever we make of this passage, it appears to drawn upon by the last chapters of the book of Revelation. For example:

  • Rev 20:8, 9 appears to allude to Zech 14:3
  • Rev 21:22-24 appears to allude to Zech 14:6
  • Rev 22:1, 2 appears to allude to Zech 14:6, 7

Again, there is very little agreement about anything more specific about these final prophecies of Zechariah.

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