Question: "Did Jesus heal two blind men (Matthew 20:29-34) or one blind man (Mark 10:46-52; Luke 18:35-43)?"
Answer: In spite of apparent discrepancies, these three passages do refer to the same incident. The Matthew account cites two men healed as Jesus left Jericho. Mark and Luke refer to only one blind man healed, but Luke says it happened as Jesus was entering Jericho while Mark records it happening as He left Jericho. There are legitimate explanations for the apparent discrepancies. Let’s look at them rather than deciding this is a contradiction and the Bible is in error.
That this is the same incident is seen in the similarity of the accounts, beginning with the two beggars sitting on the roadside. They call out to Jesus, referring to Him as “Son of David” (Matthew 20:30; Mark 10:48; Luke 18:38), and in all three accounts, they are rebuked by those nearby and told to be quiet but continue to shout out to Jesus (Matthew 20:31; Mark 10:48; Luke 18:39). The three accounts describe nearly identical conversations between Jesus and the beggars and the conclusions of the stories are also identical. The beggars receive their sight immediately and follow Jesus.
Only Mark and Luke chose to identify one of the beggars as Bartimeus, perhaps because he was the main character in the story and was therefore the sole focus of Mark’s and Luke’s accounts. Perhaps it was because Bartimeus was known to them as the son of Timeus, but the other man was a stranger to them. In any case, the fact that only one man of the two is recorded as speaking does not mean there was only one man. It simply means Mark and Luke identified only one man speaking, Bartimeus. Matthew refers to both of them calling out to Jesus, clearly indicating there were two men.
The other issue in question is whether Jesus was entering Jericho or leaving it. Bible commentators cite the fact that at that time there were two Jerichos—one the mound of the ancient city (still existing today) and the other the inhabited city of Jericho. Therefore, Jesus could have healed the two men as He was leaving the ancient city of Jericho and entering the new city of Jericho.
In any case, to focus on these minor details to the exclusion of all else is to miss the point of the story—Jesus healed the blind men, proving that He was indeed the Son of God with powers beyond anything a mortal man could have. Unlike the Pharisees who refused to see what was before their eyes, our response to Jesus should be the same as that of the blind men—call on Him to give us eyes to see spiritual truth, recognize Him for who He is, and follow Him.