What happened here (I'm pretty sure anyway - it was a totally bizarre occurance), is that I manually tweaked the Americas Cup (World Series) last season so the home-field advantage was actually in place, contrary to what the game had offered up in the schedule.
What it looks like is that the game somehow held over the schedule from the previous season and didn't clear it.
What I did was go back previous to simming the one-game playoff again, and erase the 'hidden' games that were randomly left later in the month. I then went back and simmed the one-game playoff and the rest of the playoffs then populated correctly.
This was absolutely an OOTP issue. It should not have happened. That being said, I understand that when you start tinkering with schedule, things can get a little funny. THAT being said, if OOTP actually scheduled things correctly, I wouldn't have had the problem in the first place.
Did that make any sense whatsoever?
-E