I remember when I was very young (mid-to-late 90s) playing a probably educational DOS game that was like a whole bunch of minigames. At least one of the minigames (perhaps all of them) was teddy-bear-themed. There was one involving maths, one involving a train, one involving books in a shelf (I think I remember the background graphics showing a few books on the floor which always annoyed me), and maybe there was a paint-like program I think as well. Some of this stuff might be me conflating multiple different games but I think at least most of it was from this game. I'm in the UK if that matters.
Possibly the Fun School series? https://en.wikipedia.org/wiki/Fun_School
They were popular when I was at school in the UK, early 90s. We played them on Amiga 500s but there were also DOS ports.
Fun School 4 in particular has Teddy Bear themed levels
Perhaps the Stickybear series? https://archive.org/search.php?query=4am%20stickybear
They were primarily for the Apple II but some were ported to the IBM PC.