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One possible thing to try, in my historical game I noticed that the waiver and intraleague draft events wouldn't schedule, even when I had those boxes ticked and hit save on the rules page.
I found that I needed to change another setting (e.g. increase average goals or PIM per game slightly). then save it for those drafts to work. This is all at July 1st obviously.
Also maybe try changing the number of rounds in the draft and saving.
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