The article discusses different techniques that are used in evaluating win probabilities for various college basketball bracket matchups. Ultimately, they surmise that there are too many factors that go into a game that are unquantifiable -- therefore, even with model assistance it is very difficult to increase accuracy considerably.
https://apnews.com/article/march-madness-artificial-intelligence-3b9ec0188bc8fd8361938d2fb9eb5b69