[LansdowneSt]

Change the Draft and Draft Reveal Date. I suspect it is too early and not at the OOTP 25 game default. Put the Draft at about 15 November and then the draft reveal around 15 October. This assumes, of course that 15 Oct is in the future relative to your current game date. If not, again, put Draft in November, and make the reveal tomorrow. Moving the draft reveal forward in time alone (even if keeping the draft date fixed) can trick the game into thinking it is doing last year's draft. That's the most common reason this happens.

Bottom Line, in League Settings, try resetting the draft and the draft reveal date to be a day and two days from now and try to get it to see those milestones again.