Being the head coach of UConn women's basketball team is like being the head coach of Canada's women's hockey team. Yes, you're good. Yes, you have to put a lot of work into it. Yes, there are some tough teams out there, but.... overall? There's really not much competition beyond a core group of countries/schools and you're more or less expected to win each and every year.
Granted, that speaks well for his recruiting ability, but I have to give the advantage to Wooden for recruiting and developing and repeatedly winning in a much more competitive field.