Zechariah
The King Riding on a Donkey
Zechariah pictured Zion's king arriving humble and 'riding upon an ass' rather than on a war-horse. Matthew and John present Jesus's entry into Jerusalem as the deliberate fulfillment of that image, and the prophecy's wording is fixed in a manuscript that predates Jesus by decades.
520 BC – AD 33
They Shall Look on Him Whom They Pierced
Zechariah 12:10 has the LORD declaring that Jerusalem 'shall look upon me, whom they have pierced.' A Qumran manuscript fixes that wording a century before the crucifixion. John's Gospel identifies a Roman soldier's lance-thrust at the crucified Jesus as its fulfillment, and Revelation 1:7 applies the same image to Christ's return.
300 BC – AD 33
Thirty Pieces of Silver
Centuries before the Passion, Zechariah's oracle names thirty pieces of silver, weighed as a shepherd's wage and cast to the craftsman in the house of the Lord. Matthew identifies this as fulfilled when the chief priests paid Judas that same sum, and the returned money purchased the potter's field.
400 BC – AD 33
Strike the Shepherd
Zechariah 13:7 has God's sword strike 'my shepherd' so the sheep scatter. The oracle belongs to Zechariah 9-14, composed by the Hellenistic period at the latest -- centuries before Jesus. A Qumran sect already read the verse messianically before he was born. At the Last Supper Jesus quoted it of himself, warning the Twelve they would abandon him that night, and Mark reports that they did.
300 BC – AD 33