I created similar copies of your events on a new test site and loaded the Grid template there, the sort works as expected for me there.
order_by=start_date & show_expired=false are the default values for that shortcode and so can be removed from the above if not using a different value.
Looks like you are loading a custom template, are you loading that from your themes root directory? Can you upload a copy to Pastebin or a Gist so I can test that locally?
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