at least 2 ways to do this (Very little in Calibre only has one way of doing

)
Click the
on device column head to sort (there are other ways to set the sort): Select all 2books: Right-click on the selection: Delete matching books from device:

(tip) Click the Date column (sorts by date): Locate todays (assumes the same day of the latest ADD) date: remove the tick (you want to KEEP the latest)


keyboard speed trick. After removing the first tick, LEFT Arrow:
[Begin]
down Arrow: spacebar
[Repeat] till last
Apply