Zechariah 12:2 (NIV)
I am going to make Jerusalem a cup that sends all the surrounding peoples reeling. Judah will be besieged as well as Jerusalem.
When was this fulfilled?
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Others will undoubtedly disagree, but I suggest that this prophecy has not been entirely fulfilled.
That the siege referred to in this passage does not describe the destruction of Jerusalem by Titus in AD 70 is made evident by the context of the succeeding verses.
Verse 3 acknowledges that all the nations of the earth will gather against Jerusalem, but emphasizes the injury Jerusalem will do to its attackers, not the other way around. The Lord will protect Jerusalem.
Let us consider several specifics in verses 6-10:
6 In that day will I make the governors of Judah like an hearth of fire among the wood, and like a torch of fire in a sheaf; and they shall devour all the people round about, on the right hand and on the left: and Jerusalem shall be inhabited again in her own place, even in Jerusalem.
7 The Lord also shall save the tents of Judah first, that the glory of the house of David and the glory of the inhabitants of Jerusalem do not magnify themselves against Judah.
8 In that day shall the Lord defend the inhabitants of Jerusalem; and he that is feeble among them at that day shall be as David; and the house of David shall be as God, as the angel of the Lord before them.
9 And it shall come to pass in that day, that I will seek to destroy all the nations that come against Jerusalem.
10 And I will pour upon the house of David, and upon the inhabitants of Jerusalem, the spirit of grace and of supplications: and they shall look upon me whom they have pierced, and they shall mourn for him, as one mourneth for his only son, and shall be in bitterness for him, as one that is in bitterness for his firstborn.
In verse 6 it is Jerusalem that is doing the conquering, and it is Jerusalem that will be inhabited. Jerusalem was not restored to its own place in 70; the conquest by Titus left Jerusalem uninhabited and desolate.
Verses 7 & 8 speak of the Lord defending and saving His people and that they would have the power of God with them. David was seen by the Jews as a mighty leader who rescued his people, not one who was overrun by his people's enemies.
Verse 9 - the destruction of all nations who oppose Jerusalem - did not happen in AD 70. Perhaps a partial fulfillment came in the fall of Rome four centuries later, but given the opposition continually faced by Jerusalem and those who adhere to the spiritual precepts that came from it, this appears to be a prophecy that awaits full fulfillment.
John 19:37 acknowledges the prophecy by Zechariah in verse 10, but does not claim it has been fully accomplished. That Jesus was pierced is clear. Pouring out the spirit of grace upon the people who pierced Him seems an ill-fitting description of the result of the conflict in the previous verses and the siege described in verse 2, if that siege is the one laid by Titus.
Verse 10 then has been taken by many (but not all) to refer to a glorious second coming of Jesus, in which Jerusalem is saved and beholds the resurrected Christ who bears the marks of crucifixion inflicted upon Him there in mortality. There will be siege whose results stand in stark contrast to that of AD 70.
To understand Biblical ‘prophecy’ you need to forget the western dictionary definition of that word. In ‘modern academic’ thinking, prophecy looks for a [one off] ‘fulfilment’.
Where as ‘prophecy’ in Hebraic thinking always looks for pattern. In fact it is pattern, that’s what it means. Any given prophecy may have had past, present, future fulfilment(s) - that is, Multiple. And it may also be seen to have partial fulfilment(s).
The majority of the Old Testament is prophecy. Example, the sacrificial system, Abraham sacrifices Isaac, etc.
One example (there are many)...
MAT12:40 For as Jonah was three days and three nights in the belly of a huge fish, so the Son of Man will be three days and three nights in the heart of the earth.
And, this also relates to Lazarus being raised - this was a ‘sign’ as well. (And the reason Jesus delayed going to him!). So this prophecy you quoted has already had partial fulfilment - and is right now reflecting this truth, and will in the future be fully fulfilled. Right now the heart of World events is arguably centred over Jerusalem.
So there are several answers to your Q “When was this fulfilled?” - In Nebuchadrezzar’s time, 70AD, 150BC, World War Two, Today.
This not understanding prophecy has caused discussion. Where Jesus, or an event is said to fulfil a prophecy, but the ‘event/happening’ does not seem to be related to what was spoken - the arguing being “’and then equally naively himself proceeded to apply them to situations with which they were not really connected, claiming that thereby they were ‘fulfilled’”.
Example, some may not ‘accept’ that Lazarus’s resurrection was a partial fulfilment of Jonah’ story. In ‘our thinking’ the connection many be difficult. To a Jew living in the days of the second temple, it would have been entirely normal to connect the two. The point being, my outline here may be a little difficult to accept - so I’ll just write this for consideration.
Whatever the intended meaning of Zech 12, taken as a prophecy, it has never been fulfilled; for example:
... and so forth. Thus, if this prophecy of Zech 12 has any meaning it must be about a time that is, even today, still future.
This last verse is actually the key to understanding this passage. It predicts a time when those that pierced Jesus will see Him personally. This is again predicted in 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 because of Him. So shall it be! Amen.
Thus, it appears that both Rev 1:7 and Zech 12 (esp, V10) both look forward to a time when Jesus returns and those resurrected, including the wicked will see Jesus, especially those that pierced Him.
Zech 13 continues the same prophecy and includes the prediction about the cleansing fountain that purifies from sin and iniquity, etc. While this began at Golgotha 2000 years ago, it will come to fruition in the New Jerusalem as described in Rev 22:1, "Then the angel showed me a river of the water of life, as clear as crystal, flowing from the throne of God and of the Lamb"
Thus, it appears that the prophecy of Zech 12 describes the time of Jesus return and final victory and the New Jerusalem, the details of which need not concern us here except that the Jerusalem in Zech 12 is the New Jerusalem as described in Rev 21 & 22.