Is this a text field? I think your date field from which these fields are referenced is a field of type text instead of type date.
If this were a field of type date, you should see the dates listed in ascending order as all "use values from field" value lists list their values in ascending order. That still won't be the order you want, but it's the order that you'll get with the correct field type for the field.
To get "current to oldest", you'd need to use a different method for displaying your list of dates, such as a portal inside a popover where you can click a portal row to select the value (make the field in the portal row a button). This would then allow you to sort either the relationship or the portal to get dates in descending order instead of ascending order.
I read this over several times and really do not know what I need to do. I created a portal but don't know how to add the fields inside one another.