Early Christianity recognized the allusion to Christ in the Hebrew Scriptures of Ps. 91. The impetus for this understanding undoubtedly comes from the account in the Gospels where Christ is confronted by Satan. The Tempter knew about the riddle of Gen. 3.15 and was trying to see if Jesus was the One who would crush him. The Devil guessed wrong about Jesus and caused Him to be crucified thus made Jesus a sacrifice (offered by two Jewish High Priests: Caiaphas and Annas). The crushing part will happen in the future when Christ returns. Therefore, even though the Tempter literally caused Jesus’ heel to be pierced in the crucifixion, that act demonstrated God’s love and provided a sin offering for humanity.
Since death could not hold Jesus He obtained redemption of humans through His resurrection. All who trust in Christ and His work on the cross and over the grave will see His face. The Devil made his biggest mistake by letting Jesus be crucified since it opened the door for the Spirit to indwell humans (which couldn’t happen it seems until Christ ascended the throne). 1 Cor. 2.8 speaks to this: None of the rulers of this age understood it, for if they had, they would not have crucified the Lord of glory. (NIV). This is a reference primarily to spirit entities and human rulers only secondarily. These were the powers, principalities, rulers of this dark world who mistakenly enabled Christ to redeem His people and send the Holy Spirit in their hearts as a deposit.
Here are some artistically wrought ivory book covers depicting Christ treading upon the “young lion and cobra” of Ps. 91. 13: