I'm trying to sort by the date column in this report so the transactions are in ascending order by date. Does anyone see what I'm doing wrong?

Is the date column you're sorting by the same one that you've picked for the resultset ? I ask because there are 2 called "Date" in your 2nd screenshot

From what I can tell... the highlighted portions of the 2nd and 3rd screenshots I believe confirm that?

I can't see from the second screenshot, have you got it marked as descending?

Thank you @CD, it was a different date field