I don't use that view on my Finder, but I just tried it and as soon as I clicked on Date Modified, the order changed, with divider lines between months. However in the second column where I think your picture shows, it doesn't sort at all. The only thing I can think is that in that column mode, the sort order only applies to the first column. I use the List view and there one can click on the column header to sort by that column, either up or down. Have you tried that to see if that meeds your needs?