Someone else here may be be able to cite the various passages, though I am not in the habit of reading the OT .. BUT - we did discuss this some years back and iirc I think the OT does actually say in several places, in terms (most of the OT is written in obscure phrases like that), that the messiah will be harmed and/or rejected etc.
In Psalm 22 (5th Cent. BC for the following parts) for example it says
https://en.wikipedia.org/wiki/They_have_pierced_my_hands_and_my_feet
Text of Psalm 22:16 (21:17)
This verse, which is Psalm 22:17 in the Hebrew verse numbering, reads in the Masoretic Text as: כארי ידי ורגלי, which may be read literally as "like a lion my hands and my feet". The full verse of the Masoretic text reads: כִּ֥י סְבָב֗וּנִי כְּלָ֫בִ֥ים עֲדַ֣ת מְ֭רֵעִים הִקִּיפ֑וּנִי כָּ֝אֲרִ֗י יָדַ֥י וְרַגְלָֽי (Kî sĕḇāḇûnî kĕlāḇîm 'ăḏaṯ mĕrē'îm hiqqîpûnî kā'ărî yāḏay wĕraglāy).
When translated into English, the syntactical form of this Hebrew phrase appears to be lacking a verb. In this context the phrase was commonly explained in early Rabbinical paraphrases as "they bite like a lion my hands and my feet".
The Septuagint, a Jewish translation of the Hebrew Bible into Koine Greek made before the Common Era, has "ὤρυξαν χεῗράς μου καὶ πόδας" ("they dug my hands and feet"), which Christian commentators argue could be understood in the general sense as "pierced". This reading was retained by Saint Jerome in his translation from the Greek Hexapla into the Latin of his Gallican Psalter (Foderunt manus meas et pedes meos) which was incorporated into both the Vulgate and the Divine Office.
Aquila of Sinope, a 2nd-century CE Greek convert to Christianity and later to Judaism, undertook two translations of the Psalms from Hebrew to Greek. In the first, he renders the verse "they disfigured my hands and feet"; in the second he revised this to "they have bound my hands and feet".
The Jewish Publication Society translates the phrase a "Like a lion, they are at my hands and my feet".
English translations
Some English language translations, primarily those translated by or for Christian communities, render the text as: "They have pierced my hands and my feet" although English translations are not uniform in this rendering. Versions translated outside of Christian circles, such as the Jewish Publication Society and The Judaica Press, use different English renderings based on the Hebrew text rather than the Greek.
In the book of Daniel (2nd century BC), it says this -
https://en.wikipedia.org/wiki/Old_Testament_messianic_prophecies_quoted_in_the_New_Testament
Daniel 9:24-27
And after threescore and two weeks shall Messiah be cut off, but not for himself: and the people of the prince that shall come shall destroy the city and the sanctuary;
The book of Isaiah says this -
https://en.wikipedia.org/wiki/Old_Testament_messianic_prophecies_quoted_in_the_New_Testament
Isaiah 53:5
Main article: Isaiah 53
"But he was wounded for our transgressions, he was bruised for our iniquities: the chastisement of our peace was upon him, and with his stripes we are healed." Isaiah 53:5 (King James Version)
"But he was pained because of our transgressions, crushed because of our iniquities; the chastisement of our welfare was upon him, and with his wound we were healed." Isaiah 53:5 (JPS The Judaica Press Tanakh with Rashi's commentary
Isaiah 53 is probably the most famous example claimed by Christians to be a messianic prophecy fulfilled by Jesus. It speaks of one known as the "suffering servant," who suffers because of the sins of others. Jesus is said to fulfill this prophecy through his death on the cross.[41] The verse from Isaiah 53:5 is understood by many Christians to speak of Jesus as the Messiah.
I'm also pretty sure that somewhere in the OT it talks of the Messiah, or someone very like a Messiah, being "Hung on a Tree" (and I think that's also repeated in the NT Book of ACTS) ... but someone who is more familiar with reading the OT can probably dig that one out.
Also in Psalm 22 is the following -
https://en.wikipedia.org/wiki/Psalm_22#:~:text=The original psalm (v.,portion of the composition (v.
Christianity[edit]
Christians[who?]*contend that "They have pierced my hands and my feet"*(Psalm 22:16), and "I can count all my bones"*(Psalm 22:17)*are prophecies indicating the manner of Jesus's crucifixion: that he would be nailed to a cross*(John 20:25)*and, per the Levitical requirement for a sacrifice, that none of his bones would be broken*(Numbers 9:11-13). (Christians view Jesus as an*atoning*sacrifice.)
Some Christian commentators, such as
E.W. Bullinger's Companion Bible Notes,[15]*and H A Ironside*[16]*a point out that the word use for worm in 'I am a worm and not a man'*(Psalm 26)*is 'tola'*[17]*a middle eastern worm that lives in a tree and is crushed for its red dye, also translated crimson. It is also the word used in*(Isaiah 41:14)*in the*servant songs*of Isaiah. This would be consistent with the view of the suffering person being an atoning sacrifice, dying on a tree.[18]
In the NT book of ACTS, it also says this -
https://en.wikipedia.org/wiki/Acts_1
Verses 21–22
39And we are witnesses ('martyres') of all things which He did both in the land of the Jews and in Jerusalem, whom they killed by hanging on a tree. 40Him God raised up on the third day, and showed Him openly, 41not to all the people, but to witnesses chosen before by God,