I suspect the same results would be seen on other platforms such as Linux, Chrome, and Mac.
 

Thanks for the report.  I know what's going on here and will write a detailed explanation this weekend or early next week.  Just chiming in so that no one else invests time in it.

Thanks mpearson@!

I'm assigning it to you for that write-up (not necessarily for a fix).

rnelson0@, you're entirely right that pages you haven't visited in a while are not likely to appear as omnibox suggestions.  ("URLs visited in the last 2-3 days do not seem to be a problem.")  Chrome's design requires a certain level of responsiveness for the omnibox.  As such, we cannot search all pages from your history.  Pages visited recently, pages explicitly selected from the omnibox, or pages visited a lot are searches.  Pages that have few visits, non recent, are not.

From your screenshots, it clear the (likely) only reason these URLs are being suggested at all is because they're bookmarked.  I see the star icon.  Bookmarks are always searched.  They're likely not being searched because of being in your history.  Bookmarks are suggested conservatively, which is why multiple search query suggestions can appear above them.

I'm afraid there's no easy way to fix this.  The fix would mean that URLs (bookmarked or not) that haven't been visited recently and match somewhere in a relatively obscure part of the URL (such as ?id=XYZ) would outrank search query suggestions.  Making a change like this would have too much negative fallout both in terms of performance (responsiveness) and quality; it wouldn't improve the omnibox overall.

Nonetheless, thanks for the bug report!  If you find other omnibox suggestion ordering issues, please let us know.  We do keep an eye on these reports for trends or areas in which we can actually change things for the better.

Nelson
I guess one workaround would be to bookmark those url that you commonly use. (and with some maintenance remove older bookmarks) 

Those URLs are not bookmarked - they’re individual YouTube videos or links
to specific issues in our ticket system at work. The root url for the
ticket system is bookmarked, however (YT isn’t unless that’s a default
bookmark that would persist after importing bookmarks from Firefox). Not
sure what’s up with the star, I never really even noticed that in the
results before. The links are definitely “old.”

I understand that it is not easy and probably not desireable to change the
design. I’ll just say I think that’s a shame, as that feature alone keeps
me in FF! I appreciate you taking the time to explain. Thanks!

melson0@, it really looks like those URLs are bookmarked.  The first screenshot shows a URL /view.php?id=6617 with a star icon on the left.  The second screenshot shows a long youtube URL that also has a star icon at the left.  The star icon should only appear for pages that are bookmarked.

Can you please confirm that these pages are bookmarked?  If they are not bookmarked and we're showing a star icon, that's an issue (a separate bug).  And, yes, I believe Chrome imports bookmarks from firefox.

Well, dang, I guess I bookmarked those two pages for no apparent reason. So
just past-me being dumb, not a bug :)

Even if you didn't intend to bookmark / remember you bookmarked those pages, the fact that the address bar isn't behaving as you want is our (Chrome's) problem.  We should try to make it work well regardless.  I'm sorry in this case I don't think there's anything we can do, but please report any issues you see.  thanks!