I was not expecting one person to answer but four of you did, to my surprise. Many thanks for the replies.
As @OttoKerner said:
It depends on whether those episodes were added within a certain time frame.
If you added several episodes within e.g. 12 hours, they will appear as ‘Season’ or even ‘Show’ (if the files cover several seasons)
If you added one episode alone, then this episode will appear as a single item.
And since I absolutely HATE when people just say “nvm fixed” with no other content on a forum post about a problem, here’s what I did:
- Cut the folders of the offending shows
- Pasted them into a folder that is not scanned or utilized by my Plex server
- Updated my libraries, removing the shows that had been moved from the Dashboard and the server as a whole
- Cut and Pasted them back into the folder they previously were in
- Re-updated my libraries
It’s a fairly crude way of doing it, but this seemed to fix the issue on the Dashboard.
Metadata and images have not finished re-downloading but the problem is fixed.
Hope this helps someone with the same issue in the future. 
