Knickerbocker (the narrator of both tales) tells the reader that Ichabod Crane's name (Crane) fits his physical appearance. He is very tall and skinny. He has large ears, a big nose, and feet "that might have served for shovels." He is a clownish-looking figure. Rip Van Winkle is described as a "simple, good-natured fellow." His physical appearance is not elaborated upon. Here is a difference. Rip is a meek husband, one who blends into the background. Ichabod stands out on account of his physical appearance, his huge appetite, and his gullibility in embracing all superstitions.
Both men have good rapport with the children. Rip is a constant playmate. He would play any time, shirking his own duties. Ichabod, a school teacher, is more stern in the classroom. But he would play after school and would even walk some of the children home.This was not without reward. He would go from house to house, receiving food from the students' parents. Similarly, Rip was a wanderer. He would spend time gossiping with the wives and would help neighbors often, especially if it meant avoiding his wife and his own chores. Ichabod was also a favorite, perhaps with the younger ladies, and is different from Rip in that he (Ichabod) was admired for being a scholar.
Ichabod was quite interested in supernatural tales. The narrator compares his huge appetite for food with his huge appetite for mysterious stories. He is quite gullible in this way. Rip is more interested in the day to day affairs of his town. His tastes for gossip are much more ordinary.
Ichabod directs the choir and is the school teacher. He draws people to him because of his hobbies and occupation. Rip farms his own land (occasionally) but is a town favorite as well. He doesn't draw people to him; he goes to them. Both men are fairly social and both enjoy their solitude (Ichabod with reading and Rip with hunting and fishing).
Rip is stuck with a domineering wife. Ichabod is single and actively pursues Katrina Van Tassel. This might be the largest difference between the two. Rip, a bit older, will do anything to get away from his wife. Ichabod tries to do anything to win Katrina.
Both men disappear. Of course, Rip returns after his long sleep. But this notion of disappearing is common to both stories. Note that in "The Legend of Sleepy Hollow" the narrator says that the town's preference for the supernatural has to do with how little the town changes over the years. But in Rip's case, his town has changed quite a bit in political terms. The United States has rebelled against Great Britain. Rip returns to see these changes, but he remains the same as himself. Ichabod vanishes, never to return, but it appears that Sleepy Hollow will remain the same.