I have noticed recently that shows that are already in my To Do List are not marked as already scheduled when I look at Upcoming shows for the same program.
For example, I have several college football games scheduled for today. However, when I do a search for "College Football" and then click on Upcoming, I do not see the already scheduled games marked with a check mark. I believe anything that was already in the To Do list, regardless of whether it was scheduled manually from the TiVo, via a Season Pass, or from the website, always showed up with an indicator in the Upcoming list.
I have a Roamio.