Start where the chapter starts. "The city shall be taken and the houses plundered and the women raped. Half of the city shall go out into exile" (14:2). That's Jerusalem falling, not Jerusalem rescued, and Jesus quoted it for AD 70: "Jerusalem will be trampled underfoot by the Gentiles" (Luke 21:24). Josephus records the siege, the plunder, and 97,000 captives, the unsold shipped to Egypt's mines because there was no buyer, which Moses had foretold word for word (Deuteronomy 28:68). Then verse 5: "you shall flee by the valley of my mountains." The split mountain in Zechariah is the escape route for God's people out of a city under judgment, and Jesus gave the same instruction: "flee to the mountains" (Luke 21:21). The church took it, to Pella.
The Mount of Olives is Matthew's hinge. Zechariah 14:4 is the last time the Old Testament mentions the Mount of Olives. Matthew 21:1 is the first time Matthew does, and from the moment Jesus' feet touch it everything accelerates: the entry on the donkey (Zechariah 9:9), the cleansing of the Temple, the parables of judgment, the woes, and then the Olivet Discourse itself, delivered from that mountain (24:3) about the city below it. When Jesus said "if you say to this mountain, 'Be taken up and thrown into the sea,' it will happen" (21:21), the mountain He was standing near was Olivet, the one Zechariah said would split, and F. F. Bruce saw the connection: the saying is a picture of the Day of the Lord coming swiftly. Tertullian read 14:4 the same direction, of Jesus going out "at night to the Mount of Olives" (Against Marcion 4.40). Eusebius, writing a generation after the fall of the city, read the whole chapter as "the final siege of the people by the Romans," in which "only the remnant of the people shall be saved" (Proof of the Gospel). Matthew Henry, no preterist, read the cleft mountain as the partition wall between Jew and Gentile coming down "by the destruction of Jerusalem" (Ephesians 2:14). This is not a new reading.
On "his feet will stand on the Mount of Olives," read Micah using the identical picture: "the LORD is coming out of his place, and will come down and tread upon the high places of the earth. And the mountains will melt under him, and the valleys will split open… all this is for the transgression of Jacob" (Micah 1:3–5). It was the fall of Samaria in 722 BC. Nobody saw feet. Cyril of Alexandria, in the fifth century, said 14:4 "adopts the metaphor of a noble general" taking his position over the battlefield, and John Lightfoot in 1655 said the verse "meaneth not literally Olivet's cleaving indeed or removing, but great concussions to the people, and open a way made for the enemy." That's how the prophets describe God coming in judgment on His own people, and how careful readers took it long before anyone said "AD 70." The living waters of 14:8 are the ones Jesus stood up and claimed on the last day of the Feast of Booths, the day this very chapter was read in the synagogue (John 7:37–39), and John says it was about the Spirit, who has since been given. "No more curse" in 14:11 isn't the Genesis 3 word; it's cherem, the devoted-to-destruction things of Deuteronomy 7:26, and Revelation 22:3 uses the same word for the city we live in. The chapter ends with no trader in the house of the LORD (14:21), which Jesus did with a whip, days before He told the same building it would fall. Verse 21's "those who sacrifice" is a problem for a literal future temple, not for me: "there is no longer any offering for sin" (Hebrews 10:18).
Where this is contestable: verse 4 is a reading; verses 1–2 aren't. A futurist will plant his flag on 14:4, 14:9 ("the LORD will be king over all the earth"), and 14:16 (the nations keeping Booths), and the readings I give there are defensible, not knock-downs. Verse 3's "fight against those nations" can be read "fight with those nations" (the Septuagint and Darby both have it that way, and God used Rome as He used Assyria), but I hold that as a reading, not a proof. A chapter that opens with Jerusalem captured and half exiled isn't a chapter about Jerusalem being saved from the nations; it's about the remnant being saved out of Jerusalem.
The verse-by-verse work here follows Robert E. Cruickshank Jr.'s series on Zechariah 14 and the book he and Gary DeMar wrote together, Making Prophetic Sense of Zechariah 14 (American Vision), which is where the Cyril, Lightfoot, Eusebius, Henry, and Bruce citations come from. Both men are partial preterists; I cite them for this chapter, not for everything on this site.
Read more: You've been looking where He said not to look · Chapter 9 of Ten "Future" Events · American Vision for the DeMar and Cruickshank book