Speaking anecdotally, I knew there was some form of history entry deduplication going on in the history page for quite some time, but I never knew how exactly it worked until I finally dug into the code. It seems impossible for our average user to, through using the history page, ever understand what/when we deduplicate and when we do not.
Potential ways to address this would be showing (when expanded) timestamps for deduped visits, and making the URL more prominent? I'm honestly not sure. Note that any UI update should be made across all platforms, and there are currently 3 UI implementations (Android, iOS, and everyone else).
This is also exacerbated by outstanding dedupe bugs, see crbug.com/759803, and crbug.com/763011.