How many times did Jesus predict His death?

from the old testament

• The Old Testament does not record Jesus predicting His death, but Isaiah 53 foretells the Messiah being “pierced for our transgressions” and “cut off out of the land of the living,” yet also hints at resurrection life.
• The entire sacrificial system (Leviticus 4–5; 16) pointed forward to a perfect, once-for-all sacrifice that Jesus Himself fulfilled.
• Psalm 22 vividly describes suffering, mockery, and even pierced hands and feet, anticipating Christ’s crucifixion.
• Jonah’s three days in the fish (Jonah 1:17) foreshadowed Jesus’ three days in the grave, something Jesus Himself later tied directly to His death (Matthew 12:40).

from the new testament

• Jesus' first mention of His death occurred after Peter confessed Jesus as the Christ: "From that time Jesus began to show his disciples that he must go to Jerusalem and suffer many things from the elders and chief priests and scribes, and be killed and on the third day be raised" (Matthew 16:21; cf. Mark 8:31-32, Luke 9:21-22). Matthew and Mark record that Peter rebuked Jesus for saying this (Matthew 16:22-23; Mark 8:32-33). Jesus replied to Peter, "Get behind me, Satan! You are a hindrance to me. For you are not setting your mind on the things of God, but on the things of man" (Matthew 16:23). Jesus was resolute in His mission and would not be dissuaded from enduring the cross (Hebrews 12:2; Matthew 26:36-46; Mark 14:32-42; Luke 22:39-46).
• The second time Jesus predicted His death was after the Transfiguration and after He had healed the demon possessed boy: "They went on from there and passed through Galilee. And he did not want anyone to know, for he was teaching his disciples, saying to them, 'The Son of Man is going to be delivered into the hands of men, and they will kill him. And when he is killed, after three days he will rise.' But they did not understand the saying, and were afraid to ask him" (Mark 9:30-32; cf. Matthew 17:22-23; Luke 9:43-45). Matthew says that the disciples were "greatly distressed" (Matthew 17:23). Luke adds that His disciples did not understand Him and the meaning was concealed from them.
• The third time was when Jesus told His disciples what would happen to Him as He approached Jerusalem in the final days of His life: "And as Jesus was going up to Jerusalem, he took the twelve disciples aside, and on the way he said to them, 'See we are going up to Jerusalem. And the Son of Man will be delivered over to the chief priests and scribes, and they will condemn him to death and deliver him over to the Gentiles to be mocked and flogged and crucified, and he will be raised on the third day" (Matthew 20:17-19; cf. Mark 10:32-34; Luke 18:31-34).
• The gospel of John contains other subtle references to Jesus' death (John 12:7-8; 13:33; 14:25). Jesus spoke metaphorically of His death and resurrection. In John 2:18-22 He told the Jews that He would raise up the temple, referring to His body, in three days if it was destroyed. Matthew and Luke record Jesus comparing His death and resurrection to Jonah's time in the belly of a fish: "For just as Jonah was three days and three nights in the belly of the great fish, so will the son of Man be three days and three nights in the heart of the earth" (Matthew 12: 40; cf. Matthew 16:4; Luke 11:29-32).

implications for today

Jesus came to the earth "to seek and to save the lost" (Luke 19:10). He secured salvation for those who put their trust in Him through His death and resurrection (1 Corinthians 15:3-7; John 3:16-18, 36; Ephesians 2:1-10). While His life was filled with wonderful miracles and teachings, they would have been nothing without the work of His death on the cross for the atonement of our sins and His resurrection that proved it. Jesus’ death was the sufficient sacrifice for our sins. Without His death and resurrection, He would just be another good teacher. Jesus prepared His followers for His death by communicating to them multiple times that He would die and rise again. When He died the chief priests and Pharisees, remembering that He said He would rise again, asked Pontius Pilate to put a watch over the tomb where His body was kept (Matthew 27:62-64). In predicting His death to His followers, Jesus ensured they understood His deity and His purpose for coming to Earth, especially since the Jews expected the Messiah to come as a conqueror who would free them from Roman rule. Jesus said that He came to fulfill the Law and the Prophets (Matthew 5:17), and one of the main ways He did this was through His death: His perfect sacrifice is what the sacrificial system foreshadowed (Hebrews 9—10). Jesus was the perfect, once for all, sacrifice; His worth is so great that His death covered the price for all of our sins (Romans 5:12-21).