PROBLEM: According to Luke, a blind man was healed as Jesus entered the city of Jericho (18:35), but Matthew and Mark declare that the healing took place as Jesus left the city of Jericho. Again, the accounts do not seem to be harmonious.
SOLUTION: Some believe that the healing in Luke may have actually taken place as Jesus left Jericho, claiming that it was only the initial contact that took place as “He was coming near Jericho” (Luke 18:35) and the blind man may have followed Him through the city, since he was continually begging Jesus to heal him (vv. 38–39). But this seems unlikely, since even after the healing (v. 43) the very next verse (19:1) says, “then Jesus entered and passed through Jericho.”
Still others suggest that these are two different events. Matthew and Mark clearly affirm the healing occurred as Jesus left the city (Matt. 20:29; Mark 10:46). But Luke speaks of healing one blind man as He entered the city. This is supported by the fact that Luke refers only to a “multitude” of people being present as Jesus entered the city (18:36), but both Matthew (20:29) and Mark (10:46) make a point to say there was a “great multitude” of people there by the time Jesus left the city. If the word spread of the miraculous healing on the way into the city, this would account for the swelling of the crowd. It might also explain why two blind men were waiting on the other side of the city to plead for Jesus to heal them. Perhaps the first blind man who was healed went quickly to tell his blind friends what happened to him. Or maybe the other blind men were already stationed at the other end of the city in their customary begging position. At any rate, there is no irresolvable difficulty in the passage. The two accounts can be understood in a completely compatible way.
Geisler, N. L., & Howe, T. A. (1992). When critics ask : A popular handbook on Bible difficulties (353). Wheaton, Ill.: Victor Books.