really makes me think 
Check the number of games first, the number of games correlates with the win rate also end-game items have higher wr
Think it's end of game. Which is a bad way to conceptualised the items winrate but whatever. Item winrates are one useless feature that should be avoided on DB at all cost
if you still have oov in your inventory at the end of the game, chances are that you lost.
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How are "most used items" defined?
Looking at the Riki profile under most used items it has diffusal above orb of venom and orb at a 46% win rate. I don't see how players bought diffusal more than orb unless the ranking is based on the items you have when the game ended. Is the rankings based on that? or purely how many times an item was purchased?