p.s. IF you fly a lot you’ll notice that right after the aircraft has cleared the final marker, and even as late as over the threshold, the plane will abruptly adjust cabin pressure to the exterior as the vents open up. This is normal.
So yeah, on descent, if the crew did not manage cabin pressure, there is a chance the cabin pressure would be lower than air pressure outside.
But they do ...
I find descent much more painful on the ears. It takes several minutes after landing before my ears pop (quite painfully, too) back open.