Yes, Jesus did feel pain when He was crucified. We know this because when Jesus was going about doing His ministry, He was (and still is) both man and God (John 1:1, 14; Col. 2:9). This teaching concerning His human and divine natures is called the hypostatic union. It is one of the most fundamental doctrines of the Christian faith, and it states that in the one person of Jesus were two distinct natures, the human and divine.

Logically, a human being feels pain. It is part of being who we are. Jesus, as a man, was beaten (John 18:22; 19:3). He physically had nails driven through his wrists and feet (John 19:18; Psalm 22:16; John 20:26–28). He was lifted up and hung on the cross. Like any man who was crucified back then, He felt pain. He suffered. He experienced the agony of the cross and even prayed to escape it (Luke 22:42).

Regarding the two natures of Christ is the teaching called the communicatio idiomatum. This is the doctrine that the attributes of both natures of Jesus, the human and the divine, were attributed to Him as a single person. So, for example, Jesus was thirsty (John 19:28), walked, talked, and slept, etc. These are human attributes that Jesus experienced. On the other hand, Jesus said that He would be with His disciples even to the end of the age (Matt. 28:18). This is a demonstration of His divine nature.  Here are two of the many verses that show this.

• John 19:28, “After this, Jesus, knowing that all things had already been accomplished, to fulfill the Scripture, said, ‘I am thirsty.’“
• Matthew 28:20, “teaching them to observe all that I commanded you; and lo, I am with you always, even to the end of the age.“

So, if Jesus experienced human attributes, why would He not also feel pain during His crucifixion?

But, some might say that Jesus would not feel pain because suffering is part of the fall and since you’d never sinned (1 Pet. 2:22), then he was not part of the fall and would not be subject to pain. But this argument fails because Jesus lived in a fallen world, and people afflicted Him. They harmed Him – which is why He would’ve experienced pain when He was crucified.