Zechariah wrote this incredible prediction 516 years before Jesus was born, 549 years before the event happened. We know that this prediction was written far in advance of its occurrence because the Book of Zechariah was a part of the Septuagint that was translated from Hebrew into Greek in 286 B.C. When we compare the text of this prophecy in the Septuagint with our present-day Bible, the two are identical.
The Messiah will come to Jerusalem, riding on the foal of a donkey.
Zechariah 9:9f Rejoice greatly, O daughter of Zion! Shout, O daughter of Jerusalem! Behold, your King is coming to you; He is just and having salvation, Lowly and riding on a donkey, A colt, the foal of a donkey.
New Testament Fulfillment:
Matthew 21:1-5 Now when they drew near Jerusalem, and came to Bethphage, at the Mount of Olives, then Jesus sent two disciples, saying to them, “Go into the village opposite you, and immediately you will find a donkey tied, and a colt with her. Loose them and bring them to Me. And if anyone says anything to you, you shall say, ‘The Lord has need of them,’ and immediately he will send them.” All this was done that it might be fulfilled which was spoken by the prophet (Zechariah), saying: “Tell the daughter of Zion, ‘Behold, your King is coming to you, Lowly, and sitting on a donkey, A colt, the foal of a donkey.’ ”
Matthew 21:6-11 So the disciples went and did as Jesus commanded them. They brought the donkey and the colt, laid their clothes on them, and set Him on them. And a very great multitude spread their clothes on the road; others cut down branches from the trees and spread them on the road. Then the multitudes who went before and those who followed cried out, saying: “Hosanna to the Son of David! ‘Blessed is He who comes in the name of the LORD!’ Hosanna in the highest!” And when He had come into Jerusalem, all the city was moved, saying, “Who is this?” So the multitudes said, “This is Jesus, the prophet from Nazareth of Galilee.”
We know, from history that Zechariah lived and wrote in the second year of Darius I, King of Persia; twenty-eighth years from Amyntas, king of Macedon; in the Seventh year of Demaratus, king of Lacedaemon, of the family of the Proclidae; in the Eleventh year of Cleomenes, king of Lacedaemon, of the family of the Eurysthenidae; in the Fifteenth year of Tarquinius Superbus, the last king of the Romans. This was about twelve years before the commencement of the consular government. 
The ability to accurately date this prophecy, over five hundred years before the events occurred, makes this prophecy even more stunning. When we team Zechariah’s prophecy with Daniel Chapter 9:24-27, the detail and clarity of these events, that would transpire in the ministry of the Messiah, take on a cosmic importance. How could two prophets writing from different locations, at different periods of history, speak of the same future events of the Messiah with such precision and detail? Every word of their prophetic utterance came about precisely as they foretold.
The following study from Daniel 9:24-27 is also found in the chapter: “Arrival of the Messiah.” I have included a brief description of the text from this prophecy as it applies to Zechariah 9:9.
Daniel is writing chapter 9 of his prophecy from Babylon in 538 B.C., while Zechariah is writing his prophetic words in 549 B.C., from Jerusalem—after the return of the Jews who had been held in Babylon. The Jews came back to their homeland in the eighth month of Darius’ second year, which was October-November, 520 B.C. This was the year that the foundation for the Temple was laid, being completed just three years later in 517 B.C. This expeditious completion was due to the encouragement of Zechariah and Haggai. For more information see the detailed timeline chart in Arrival of the Messiah.
Daniel 9:25 Know therefore and understand, That from the going forth of the command To restore and build Jerusalem Until Messiah the Prince, There shall be seven weeks and sixty-two weeks; The street shall be built again, and the wall, Even in troublesome times.
The principle of a prophetic week is first illustrated in the Book of Genesis Chapter 29. As Jacob desires Rachel’s hand in marriage, he does not have the dowry required to pay Rachel’s father Laban. The purpose of a dowry was Alimony in advance. If a man should desire to marry a young woman and later divorce her without any financial support, her dowry, kept in the stewardship of her father, would serve as her support. Therefore, Rachel’s father Laban brokered a deal with Jacob in which he would work for him as a servant for seven years to pay for Rachel’s dowry.
After seven years when Rachel should have come to Jacob on their wedding night, Laban sends his oldest daughter Leah into the darkness of the bridal tent. As the marriage is consummated, the next morning Jacob realized that he has been with Leah, not Rachel. When he confronts Laban, Jacob learns that in their tradition, the oldest daughter must marry first before the younger. Laban tells Jacob to “fulfill the week” of Rachel, and he can have her also as his wife. At the end of verse 27, Laban defines how long this week will be by saying “serve with me still another seven years.”
Genesis 29:27 Fulfill her week, and we will give you this one also for the service which you will serve with me still another seven years.
From this definition in Genesis 29, we understand that Daniel is describing seventy weeks as seventy, seven year periods, or 490 years (70 X 7 = 490).
In Daniel 9:25 the Lord is giving Israel the precise day that the Messiah will arrive. This prophecy is a companion to Zechariah 9:9, as both speak of the first arrival of the Messiah, when He announces the fulfillment of Daniel and Zechariah’s prophecies at Jerusalem.
- First, a command will be given, then seven weeks and sixty two weeks (69 weeks of years, 483) will pass “until the Messiah, the Prince” will come.
- In the first seven weeks (49 years), the Temple will be rebuilt in Jerusalem.
- Second, At the conclusion of the sixty-two weeks (434 years), the Messiah will arrive.
The trigger to begin the countdown of this prophecy is the command to restore and build Jerusalem.
Let’s do the math:
- The prophecy is for 69 times seven (69×7) years, or a total of 483 years.
- Encyclopedia Britannica records that Artaxerxes Longimanus issued this decree to release the captives of Israel in Babylon, on March 14, 445 B.C.
- The Babylonian calendar was based upon a 360-day per year cycle.
- 360 days per year multiplied by 483 years equals 173,880 days.
- Taking into account the calendar year change over from 1 B.C. to 1 A.D. because there is no “0” year.
- Adding 116 days for leap years.
- 173,880 days added to March 14, 445 B.C.
- We come to the date of April 6th, the year 32 A.D.
Was there any event of particular importance that occurred on April 6, 32 A.D.? Luke records that on this day, Jesus instructed His disciples to go over to Bethphage and bring Him the foal of a donkey…
Luke 19:29-42 And it came to pass, when Jesus came near to Bethphage and Bethany, at the mountain called Olivet, that He sent two of His disciples, saying, “Go into the village opposite you, where as you enter you will find a colt tied, on which no one has ever sat. Loose him and bring him here. And if anyone asks you, ‘Why are you loosing it?’ thus you shall say to him, ‘Because the Lord has need of it.’ ” So those who were sent went their way and found it just as He had said to them. But as they were loosing the colt, the owners of it said to them, “Why are you loosing the colt?” And they said, “The Lord has need of him.” Then they brought him to Jesus. And they threw their own clothes on the colt, and they set Jesus on him.
This is the same donkey that Zechariah 9:9 is speaking of.
“…your King is coming to you; He is just and having salvation, Lowly and riding on a donkey, A colt, the foal of a donkey…”
Consider that Jesus specifically instructs the disciples to bring the foal—not an older, more mature donkey. A foal is an unbroken young animal that has never had a man upon his back. Under normal circumstance, this young donkey would throw-off the first person that attempted to sit upon his back. Incredibly, Jesus rides this foal into Jerusalem on this day and allows the assembled crowd to hail Him as “The Son of David,” a clear title for the Messiah.
Matthew 21:8-9 And a very great multitude spread their clothes on the road; others cut down branches from the trees and spread them on the road. Then the multitudes who went before and those who followed cried out, saying: “Hosanna to the Son of David! ‘Blessed is He who comes in the name of the LORD!’ Hosanna in the highest!”
It is interesting that up to this point Jesus had refused all requests by His disciples that He would announce to the world that He was the promised Messiah. Jesus had repeatedly told them: “My time has not yet come.”
John 7:3-6 His brothers therefore said to Him, “Depart from here and go into Judea, that Your disciples also may see the works that You are doing. For no one does anything in secret while he himself seeks to be known openly. If You do these things, show Yourself to the world.” For even His brothers did not believe in Him. Then Jesus said to them, “My time has not yet come, but your time is always ready.”
Jesus was waiting for this one, specific day when Daniel and Zechariah predicted that the Messiah would come to Jerusalem.
There was no mistake in what the people were proclaiming about Jesus. The crowd was shouting, “Hosanna to the Son of David.” The Pharisees understood what the people meant by these words: they believed that Jesus was the promised Messiah, and He was receiving their praise in acceptance of this truth.
Luke 19:39-42 And some of the Pharisees called to Him from the crowd, “Teacher, rebuke Your disciples.” But He answered and said to them, “I tell you that if these should keep silent, the stones would immediately cry out.” Now as He drew near, He saw the city and wept over it, saying, “If you had known, even you, especially in this your day, the things that make for your peace! But now they are hidden from your eyes.”
Jesus told the Pharisees, “If you had known this your day…”
“This day” was one unique day in the history of the universe, when the Son of God would come to Jerusalem and be hailed as the Messiah. The Book of Psalms has a specific text that David wrote for this precise day.
Psalms 118:24-26 This is the day the LORD has made; We will rejoice and be glad in it. Save now, I pray, O LORD; O LORD, I pray, send now prosperity. Blessed is he who comes in the name of the LORD!
This verse of prophetic scripture was written for one particular day in all of time and Eternity. It was written for the moment when the Messiah would come to Jerusalem and be recognized as the Messiah, who would fulfill all of the Old Testament prophecies. Psalm 118 contains the language, “save now” and “Blessed is He who comes in the name of the LORD,” because this is what those present when the Messiah arrived, would proclaim with their shouts of praise. The people who had gathered to greet Jesus as the Messiah were well aware of Psalm 118, and this is why they were reciting these specific words as Jesus made His entrance into the city.
On April 6th, 32 A.D., Jesus rides upon the foal of a donkey into Jerusalem and is proclaimed the “Son of David,” the Messiah, thus fulfilling the prophecies of Daniel Chapter 9 and Zechariah Chapter 9.
Zechariah 9:9 Rejoice greatly, O daughter of Zion. Shout, O daughter of Jerusalem! Behold, your King is coming to you; He is just and having salvation, Lowly and riding on a donkey, A colt, the foal of a donkey.
Zechariah wrote this prophecy of the Messiah’s arrival at Jerusalem, about 516 years before Jesus came into Jerusalem on this specific Palm Sunday. Daniel’s prophecy of the precise day the Messiah would come to Jerusalem, was written almost 549 years before Jesus arrived.
When a king made his entrance into a city and his purpose was to conquer, he always rode on the back of a great white stallion (Revelation 19:11). When a king was arriving in “peace,” he would ride on the back of a humble donkey. Jesus was appearing in Jerusalem in fulfillment of Daniel’s prophecy. He was coming to proclaim the time when men can make peace with God by experiencing the forgiveness of their sins.
The Bible has revealed the precise day that the Messiah would arrive on the earth, the first time, as Savior and Lord. This is, however, not the end of this story. After His arrival, the elders of Israel would reject Him as the Messiah and crucify Him, just as the scriptures foretold.
This type of verifiable, prophetic evidence, is a stunning proof for the authenticity of the Bible and should cause any reasonable person to conclude that the men who wrote these prophecies, as well as those who recorded their fulfillment, are honest men.
 Adam Clarke’s Commentary on the Old Testament.
 Encyclopedia Britannica, 1990 Edition