This might be a little “meat not milk (Hebrews 5)” study. A little advanced math (Calculus). Many say Zechariah 14:4 has not been fulfilled yet, that it will be fulfilled when Jesus comes back at some time in the future. ⁴ On 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 forming a very large valley. Half of the mountain will move toward the north, and the other half toward the south.” In contrast, I think all of the predictions in Zech 9-14 were fulfilled in the destruction of the temple and of Jerusalem in 70 AD by the Romans.

To begin with: In Luke 21:22 Jesus said that, ²⁰ “But when you see Jerusalem surrounded by armies, ²² because these are days of punishment, so that all things which have been written will be fulfilled. That would be “all things written, including prophesies, in the Old Testament”. This would happen within the generation of those he was speaking to. Luke 21:³² Truly I say to you, this generation will not pass away until all things take place.” The Greek word genea as used in the NT always means a 40 year period or the people living in a 40 year period. The “Jerusalem surrounded by armies would have to happen within that generation, and it did in 70 AD when the Romans sieged and destroyed Jerusalem. I quote all this in Luke 21 b/c that means that everything in Zechariah 9-14 must be fulfilled by 70 AD according to Jesus. Not “some predictions” but “all predictions” in the OT had to be fulfilled by 70 AD or else Jesus is a false prophet.

Now to Zechariah 9-14 and specific predictions that were fulfilled by 70 AD. BTW an excellent video on this by Alex Polyak thebiblefulfilled.com He has many videos that are great. Check it out!

1. Zech 9:9 Rejoice greatly, daughter of Zion! Shout in triumph, daughter of Jerusalem! Behold, your king is coming to you; He is righteous and endowed with salvation, Humble, and mounted on a donkey, Even on a colt, the foal of a donkey.” Fulfilled when Jesus rode into Jerusalem on a donkey.
2. Zech 11:1 Open your doors, Lebanon, So that a fire may feed on your cedars. ² Wail, juniper, because the cedar has fallen, For the magnificent trees have been destroyed.” Polyak says this was fulfilled in 70 AD. The temple in Jerusalem was built with cedars from nearby Lebanon. So the “fires feeding and destroying” the cedar timbers would be the fire that destroyed the temple in 70 AD.
3. Zech 11:⁹ Then I said, “I will not pasture you. What is to die, let it die, and what is to perish, let it perish; and let those who are left eat one another’s flesh.” Josephus tells of a well known, rich Jewish woman who cooked and ate her baby during the siege of Jerusalem in 70 AD. The Romans cut off all food to the city and starvation lead to cannibalism
4. Zech 11:¹⁰ And I took my staff Favor and cut it in pieces, to break my covenant which I had made with all the peoples. ¹¹ So it was broken on that day, and so the afflicted of the flock who were watching me realized that it was the word of the Lord.” The end of the Jewish Age and of the old covenant was in 70 AD. Hebrews 8:¹³ When He said, “A new covenant (Jeremiah 31:31-34),” He has made the first obsolete. But whatever is becoming obsolete and growing old is about to disappear.” That was written in about 62 AD. The old covenant was “broken” and disappeared in 70 AD.
5. Zech 11:¹³ Then the Lord said to me, “Throw it to the potter, that magnificent price at which I was valued by them.” So I took the thirty shekels of silver and threw them to the potter in the house of the Lord.” This was the money Judas received to betray Jesus but which he threw back in the temple. The money was used to buy a potter’s field to bury poor people.
6. Zech 12:² “Behold, I am going to make Jerusalem a cup that causes staggering to all the peoples around; and when the siege is against Jerusalem, it will also be against Judah. ³ It will come about on that day that I will make Jerusalem a heavy stone for all the peoples; all who lift it will injure themselves severely. And all the nations of the earth will be gathered against it.” This would be the siege of Jerusalem by the Romans (“all the nations gathered against it”) in 70 AD.
7. Zech 12:⁸ On that day the Lord will protect the inhabitants of Jerusalem, and the one who is feeble among them on that day will be like David, and the house of David will be like God, like the angel of the Lord before them. ⁹ And on that day I will seek to destroy all the nations that come against Jerusalem.” I believe this is the saving of the remnant who heeded Jesus’ words in Matthew 24 to flee the city when they had the opportunity (before the final siege in 70 AD). History (Eusebeus) records that the Jewish Christians in the city fled safely to Pella . But how were the nations the sieged the city (i.e. the Romans) “destroyed” in 70 AD. Not physcially. Jesus said in John 18:³⁶ Jesus answered, “My kingdom is not of this world. If My kingdom were of this world, My servants would be fighting so that I would not be handed over to the Jews; but as it is, My kingdom is not of this realm.” So we do not expect “The kingdom of the world has become the kingdom of our Lord and of His Christ; and He will reign forever and ever (Revelation 11:15)” to be a physical destruction of the kingdom of Rome. Instead, it was the demonic prince of the kingdom of Rome that was destroyed in 70 AD, as well as all the demonic princes of all the kingdoms of the world. This ideas is supported by Rev 16:¹⁴ for they are spirits of demons, performing signs, which go out to the kings of the entire world, to gather them together for the war of the great day of God, the Almighty.” It was the demons of the kingdoms that would be destroyed in 70 AD.
8. Zech 12:¹⁰ “And I will pour out on the house of David and on the inhabitants of Jerusalem the Spirit of grace and of pleading, so that they will look at Me whom they pierced; and they will mourn for Him, like one mourning for an only son, and they will weep bitterly over Him like the bitter weeping over a firstborn. ¹¹ On that day the mourning in Jerusalem will be great, like the mourning of Hadadrimmon in the plain of Megiddo.” Jesus was pierced on the cross with nails and then a spear. But this passage refers to the mourning of the Jews when the temple was being destroyed in 70 AD. The book of Revelation was written about 63-65 AD, predicting things that would “shortly take place” (Rev 1:1-3; 22:4-10). Rev 1:⁷ Behold, He is coming with the clouds, and every eye will see Him, even those who pierced Him; and all the tribes of the earth will mourn over Him. So it is to be.” So the mounring of the Jews would be at the 2nd coming in 70 AD as they endured a horrible “tribulation” of suffering and the destruction of their beloved temple. This would occur at 70 AD. “Armageddon” (“hill of Megido”) in only mentioned once, in Rev 16:¹⁴ for they are spirits of demons, performing signs, which go out to the kings of the entire world, to gather them together for the war of the great day of God, the Almighty. ¹⁵ (“Behold, I am coming like a thief. Blessed is the one who stays awake and keeps his clothes, so that he will not walk about naked and people will not see his shame.”) ¹⁶ And they gathered them together to the place which in Hebrew is called Har-Magedon (or Armageddon).” Megiddo was an ancient city in Palestine that was the site of many military encounters due to its strategic location. In Rev 16:16 and Zech 12:11 it refers to 70 AD. All the events predicted in Revelation had to happen “shortly” after the time of writing, so Armageddon had to be 70 AD and not some final war still in our future as many claim. Jesus also predicted the mourning of the Jews in 70 AD in Matthew 24:³⁰ And then the sign of the Son of Man will appear in the sky, and then all the tribes of the earth will mourn, and they will see the Son of Man coming on the clouds of the sky with power and great glory.” That had to be fulfilled within that generation, so it had to be 70 AD. Matthew 24:³⁴ Truly I say to you, this generation will not pass away until all these things take place.” The Jews still mourn at the “waiting wall” over the destruction ofJerusalem in 70 AD. Tisha B’Av is a day of fasting, mourning, and reflection that commemorates the destruction (in 70 AD) of the Second Temple in Jerusalem. It’s considered the saddest day in the Jewish calendar. 
9. Zech 13:1 “On that day a fountain will be opened for the house of David and for the inhabitants of Jerusalem, for sin and for defilement.” This would be a fountain of living water (John 4:¹³ Jesus answered and said to her, “Everyone who drinks of this water will be thirsty again; ¹⁴ but whoever drinks of the water that I will give him shall never be thirsty; but the water that I will give him will become in him a fountain of water springing up to eternal life”) provided for the remnant who accepted Jesus as the Messiah before 70 AD. Rev 22:1 And he showed me a river of the water of life, clear as crystal, coming from the throne of God and of the Lamb.” This fountain of living water came from the new Jerusalem, the church, the bride of Christ, that would replace the old Jerusalem which was destroyed in 70 AD (Rev 21). That new Jerusalem would come down out of heaven to earth, providing this living water (Rev 21:1).
10. Zech 13:7 “Awake, sword, against My Shepherd, And against the Man, My Associate,” Declares the Lord of armies. “Strike the Shepherd and the sheep will be scattered”. Jesus and Matthew said this was fulfilled when the disciples fled to a home after the arrest of Jesus in the Garden.
11. Zech 13:8 And it will come about in all the land,” Declares the Lord, “That two parts in it will be cut off and perish; But the third will be left in it. ⁹ And I will bring the third part through the fire, Refine them as silver is refined, And test them as gold is tested. They will call on My name, And I will answer them; I will say, ‘They are My people,’ And they will say, ‘The Lord is my God.’” The 2/3 that would be destroyed would be the million Jews destroyed in the siege of Jerusalem in 70 AD. The 1/3 would be the remnant that escaped to Pella, but they would be tested by fire to refine them in the tribulation of 70 AD (Matthew 24:21; Daniel 12:1-3). Peter speaks of the diaspora Jewish Christians being tested by fire with trials for a “little while” before being saved (1 Peter 1).
12. Zech 14:1 Behold, a day is coming for the Lord when the spoils taken from you will be divided among you. ² For I will gather all the nations against Jerusalem to battle, and the city will be taken, the houses plundered, the women raped, and half of the city exiled, but the rest of the people will not be eliminated from the city.” Remember Luke 21:22 “all the things that have been written will be fulfilled” within the generation Jesus was speaking to (Luke 21:³² Truly I say to you, this generation will not pass away until all things take place.) So the events in Zechariah 14 had to be fulfilled in the first century AD and 14:1 is the Roman nations gathered to destroy Jerusalem in 70 AD.
13. Zech 14:³ Then the Lord will go forth and fight against those nations, as when He fights on a day of battle. ⁴ On 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 forming a very large valley. Half of the mountain will move toward the north, and the other half toward the south. ⁵ And you 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 from the earthquake in the days of Uzziah king of Judah. Then the Lord, my God, will come, and all the holy ones with Him!” this is not to be fulfilled literally with the Mount of Olives literally being split when Jesus comes back in our future. It had to be fulfilled within the generation Jesus spoke to (Luke 21:22,32). It does happen figuratively at Jesus’ 2nd coming in 70 AD. That event would be “earthshaking”, cataclysmic. Thus the splitting of the Mount of Olives figure. Even though the Romans destroyed Jerusalem, God will then destroy the demonic prince of Rome (Rev 16:16) at the battle of Armageddon in 70 AD. The remnant of Jewish Christians in the city would flee to Pella for safety just as Jesus told the to in Matthew 24.
14. Zech 14:⁶ On that day there will be no light; the luminaries will die out. ⁷ For it will be a unique day which is known to the Lord, neither day nor night, but it will come about that at the time of evening there will be light.” This was fulfilled in the new Jerusalem, the church, the bride of Christ. Rev 21:²³ And the city has no need of the sun or of the moon to shine on it, for the glory of God has illuminated it, and its lamp is the Lamb. ²⁴ The nations will walk by its light, and the kings of the earth will bring their glory into it. ²⁵ In the daytime (for there will be no night there) its gates will never be closed; ²⁶ and they will bring the glory and the honor of the nations into it.”
    
15. Zech 14:⁸ And on 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.” As in Zech 13:1 and Rev 22:1 the living water of eternal life (John 4:13; 7:37) will flow out of the new Jerusalem, which is the church, the bride of Christ (Rev 21). This is the same water flowing from Ezekiel’s Messianic temple and new Jerusalem in Ezekiel 47:1 Then he brought me back to the door of the house; and behold, water was flowing from under the threshold of the house toward the east, for the house faced east. And the water was flowing down from under, from the right side of the house, from south of the altar. ² And he brought me out by way of the north gate and led me around ^[a]on the outside to the outer gate, by the way facing east. And behold, water was spurting out from the south side.” That living water would give life everywhere it flowed. Ezekiel 47:⁶ And he said to me, “Son of man, have you seen this?” Then he brought me back to the bank of the river. ⁷ Now when I had returned, behold, on the bank of the river there were very many trees on the one side and on the other. ⁸ Then he said to me, “These waters go out toward the eastern region and go down into the Arabah; then they go toward the sea, being made to flow into the sea, and the waters of the sea become fresh. ⁹ And it will come about that every living creature which swarms in every place where the river goes, will live. And there will be very many fish, for these waters go there and the others become fresh; so everything will live where the river goes.” This is not some 3rd temple that Jews and many Christians expect to be built in our future. In the new Jerusalem that came down from heaven to earth (Rev 21:1), which is the bride of Christ, the church (Rev 21:9-10) that would “shortly happen” (Rev 21:1-3; 22:5,10) there would be no temple for the Lord is the temple. Rev 21:²² I saw no temple in it (i.e. the new Jerusalem 21:10), for the Lord God the Almighty and the Lamb are its temple.” There is no 3rd temple to be built someday. This beautiful passage closes out the last chapter of Revelation and sums up the predictions in Zechariah 13:1; 14:6-8, and Ezekiel 47,48. Revelation 22:1 And he showed me a river of the water of life, clear as crystal, coming from the throne of God and of the Lamb, ² in the middle of its street. On either side of the river was the tree of life, bearing twelve kinds of fruit, yielding its fruit every month; and the leaves of the tree were for the healing of the nations. ³ There will no longer be any curse; and the throne of God and of the Lamb will be in it, and His bond-servants will serve Him; ⁴ they will see His face, and His name will be on their foreheads. ⁵ And there will no longer be any night; and they will not have need of the light of a lamp nor the light of the sun, because the Lord God will illuminate them; and they will reign forever and ever.” Everything lost in the Garden (Paradise Lost by John Milton) would be restored figuratively with the living water, trees that bear fruit year round (i.e. Christians), no more curse from the Fall in the Garden, no more night for the Lord is our Light.
16. Zech 14:¹⁶ Then it will come about that any who are left of all the nations that came against Jerusalem will go up from year to year to worship the King, the Lord of armies, and to celebrate the Feast of Booths. ¹⁷ And it will be that whichever of the families of the earth does not go up to Jerusalem to worship the King, the Lord of armies, there will be no rain on them. ¹⁸ And if the family of Egypt does not go up or enter, then no rain will fall on them; it will be the plague with which the Lord strikes the nations that do not go up to celebrate the Feast of Booths. ¹⁹ This will be the punishment of Egypt, and the punishment of all the nations that do not go up to celebrate the Feast of Booths.” The Romans would destroy Jerusalem in 70 AD but God would then judge the Romans with spiritual death (figuratively a “plague” 14:14). But some of the nations (Romans) would start worshipping Yeshua and Yahweh the King of Kings yearly at the Feast of Booths. That would be Gentile Christians who would start worshipping Jesus. We know the Feast of Booths (Tabernacles) was a shadow of the new covenant and certainly not binding on Gentile Christians in the new covenant. So this must be figurative, using the terminology of the old covenant worship but really meaning the true new covenant worship and not the old covenant shadows. This is typical of Messianic predictions. Jeremiah said that in the Messianic Age David would be king and prince (fulfilled in Jesus) and there would always be Levitical priests to offer burnt offerings (Jeremiah 33:17). Again, we know the Levitical priesthood and burnt offerings were done away with in the new covenant so this can’t be literal. It must be figurative using old covenant worhip terminology but really meaning worship in the new covenant.

That concludes my Zechariah 9-12 comments. There are still a lot of verses in those chapters that I don’t understand, but I think all of it was fulfilled by 70 AD b/c of Luke 21:21-22. Zechariah prophesied about 500 years before 70 AD, so that is amazing fulfilled prophecy, which is God’s #1 way of proving that He is the one true God.