Looks like I'll be able to keep this thread going for a while longer, since OOTP is managing to screw up pretty much every single league.

Here's the next one:
Atlantic League South, first half:
CAM 33-30
SOM 30-33
ACS 26-37
LAN 21-42
CAM declared the first-half winner.
full season:
CAM 61-65 (the other division has a .700 team, oops)
ACS 56-70
LAN 56-70
SOM 52-74
Guess who's now listed as the half-season winner...SOM (!) - and in fact, this time the bogus change happened within the season. It was still correct on Sep 4th, but already wrong on Sep 24th before the final day's games. The playoff spots went to CAM and SOM. Well, I guess CAM at least didn't get cheated out of the playoffs, but the SOM pick is totally unfathomable to me.
So, that's one simmed season with 5 leagues, and 3 of them managed to have nonsensical playoff picks. I shudder to think what I'd find if I simmed for any more data.
Edit: And yet another one, still from the same season. This is the Atlantic League's rookie affiliate that I have in my universe.
first half:
ACS-R 28-21
LAN-R 28-21
SOM-R 27-22
BRI-R 24-25
CAM-R 23-26
LID-R 23-26
PEN-R 22-27
NEW-R 21-28
LAN-R was declared the first-half champion. By the end of the season, that designation has mysteriously moved over to BRI-R who aren't even the overall winners either, just like the main Atlantic League's case with SOM:
ACS-R 57-41
LAN-R 56-42
BRI-R 51-47
NEW-R 47-51
PEN-R 46-52
SOM-R 46-52
LID-R 45-53
CAM-R 44-54