Yes, this is a known problem - if you have two flights on one day (or by the look of what you have posted, if you have two flights credited on one day) where a status threashold is crossed, the first flight's status miles get flagged and adjusted (probably manually?) but the second one seems to get lost.

You'll need to contact Diamond Club to ahve this fixed. It won't be a struggle, as this is a well-known and well-documented problem.

This may be fixed by their new admin system, but I would contact DC immediately, before everything goes in to stasis.