Further to my last post I’ve also just experienced a Calendar Widget update issue, the event was for 1Hrs this morning which was showing in “Up Next” until that time when it duly showed in Calendar for the Hrs after which it disappeared - because the event had past that’s what you would expect to happen. But while this was happening the “Up Next” didn’t update, it still showed that “past” event when in fact it should have been the next future event some 7 days time.
I also have an iPad Mini 2 setup similar to the iPhone so went and checked and that appears to display correctly, ie. no event now in Calendar Widget and the new future one now in the Up Next Widget.
No amount of scrolling or moving in/out of the Widget Screen made any difference, even turning off/on the WiFi to force the use of cellular for a while failed to update - last try was a Force Restart and this sorted (or unstuck things), but not sure yet how long that will last.
So like with the Weather Widget and some third party ones, it looks like certain devices are having issue with the Widget Screen updating - the iPhone X certainly seems more prone to this in my experience at the moment.
Whether “Up Next” would have eventually updated without the Force Restart I’m not sure (like the Weather and the third party do) but when/if it happens again will just leave and see.