Maybe I am missing something and this is a very dumb report.
My instinct is that with Sort Date (New to Old), the list should be sorted with the elements with closer deadline first and farther deadline last.
The list
* b !(2020-05-28)
* a !(2020-05-27)
* c !(2020-05-29)
after sort date (new to old), becomes:
c !(2020-05-29)
b !(2020-05-28)
a !(2020-05-27)
expected results
* a !(2020-05-27)
* b !(2020-05-28)
* c !(2020-05-29)