Culled From: http://infidels.org/library/modern/jim_lippard/fabulous-prophecies.html
Christian apologists are perhaps most impressed by a number of alleged prophecies relating to Jesus' crucifixion. They claim that the Hebrew scriptures contain prophecies that Jesus would be crucified, that his garments would be divided by the casting of lots, that he would be given wine mixed with gall or myrrh, that he would cry out about being forsaken, and that none of his bones would be broken. There are several verses taken to refer to crucifixion: Psalms 22:16, Zechariah 12:10, and Zechariah 13:6 are typical examples. Psalms 22:16 reads, "For dogs have surrounded me; a band of evildoers has encompassed me; they pierced my hands and my feet." This is a psalm of David which gives no indication of being prophetic and which describes the speaker being hunted down and killed rather than being crucified. Gerald Sigal (1981, p. 98) argues that the Hebrew word translated here as "pierced" is "ariy," which means "lion," and so a more accurate translation would be "like a lion [they are gnawing at] my hands and feet." Gleason Archer (1982, p. 37), however, argues that "they pierced" is correct, based on the Septuagint's translation and other considerations.
Zechariah 12:10 says "they will look on me whom they have pierced; and they will mourn for him, as one mourns for an only son ...." The gospel of John (19:37) takes this as prophecy fulfilled by Jesus' crucifixion, but there is no indication that this speaks of crucifixion. Further, the "him" being mourned for is not the "me" that is being pierced. The Jewish interpretation of this verse is that God is speaking of the people of Israel being "pierced" or attacked (Sigal 1981, pp. 80-82).
Zechariah 13:6 speaks of "these wounds between your arms," spoken of one who claims not to be a prophet and to have been sold as a slave in his youth (Zechariah 13:5). Wounds between one's arms are not characteristic of crucifixion, and Jesus was neither sold as a slave nor claimed not to be a prophet.
Only the gospel of John speaks of Jesus' garments being divided among the soldiers and their casting of lots for his tunic (John 19:23-24), and he cites (Psalms 22:18 as the prophecy which is thereby fulfilled. This latter verse reads, "They divide my garments among them, and for my clothing they cast lots." This verse tells of one event--clothing being divided by the casting of lots. But John transforms it into two events: first the division of Jesus' clothing apart from his tunic (John 19:23) and then casting of lots for his tunic (John 19:24). It appears that John created a story in an attempt to provide a fulfillment for his misunderstanding of a verse which gives no indication of being a prophecy in the first place.
Matthew (27:34) speaks of Jesus being given "wine to drink mingled with gall" and Mark (15:23) says he was offered "wine mixed with myrrh." These are both taken to be references to Psalms 69:21, which says "they gave me gall for my food, and for my thirst they gave me vinegar to drink." The Hebrew word here translated as "gall" is "rosh," meaning poison or gall, and referring to some poisonous plant. The verse says that poison is being put into food, which does not apply to the crucifixion. Myrrh, which is not poisonous, is referred to by the Hebrew word "mor," which does not appear in Psalms 69:21. This psalm, which speaks repeatedly of flood waters, gives no indication of being either prophetic or of applying to Jesus.
The gospels of Matthew (27:46) and Mark (15:34) give Jesus' last words as "My God, my God, why hast thou forsaken me," a quotation of Psalms 22:1. Luke (23:46) gives "Father, into thy hands I commit my spirit" as Jesus' final words, while John (19:30) has Jesus say "It is finished." Only the first of these is claimed to be fulfillment of prophecy, yet it is hardly miraculous that Jesus would make such a statement. Presumably Jesus was familiar with the Hebrew scriptures. Such a remark, however, is inconsistent with Christian theology. Why would Jesus, supposed to be God incarnate, speak of being forsaken by himself at all, let alone at the culmination of his plan for human salvation? It is also not apparent that Psalms 22 is either prophetic or applicable to Jesus (see Sigal 1981, pp. 95-99).
A final prophecy I wish to examine relating to the crucifixion is that Jesus' bones would not be broken. It is only the gospel of John (19:32-36) which tells of soldiers breaking the legs of the crucifixion victims to hasten their deaths, yet sparing Jesus because he was already dead. John 19:36 cites Psalms 34:20, "He keeps all his bones; not one of them is broken," as the prophecy which is thereby fulfilled. There is no indication that Psalms 34 is intended as prophetic, nor that it applies to Jesus. The intent in the gospel of John is to represent Jesus as a sacrifice, specifically corresponding to the paschal lamb (e.g., John 1:29, 36). A requirement of the paschal lamb is that none of its bones be broken (Exodus 12:46, Numbers 9:12). But this analogy fails for several reasons: the paschal lamb was not for the atonement of sin, and Jewish sacrifices were required to be completely without blemish, sore, or injury (Leviticus 22:20-25) while Jesus was scourged and mutilated (John 19:1; Sigal 1981, pp. 265-268).