I’m not sure what the right solution is, but could a data point on the right of each entry be added, or some other change be made to make it clear what order the data points were added, even when all shown points were submitted on the same day?
To be completely honest, I don’t like a lot of things about this screen, like the leading numbers on this screen.
The fact that the only indication that the 31 is part of the date is at the very bottom of the screen really, really irks me.
I would like to think about bringing the data entry above the data point list, and sort them so that when you submit a datapoint, the data point goes to the top of the list, and the rest shift down. I think this may even help with your “which is newest” issue.
My first thought is: Let’s ensure that the datapoints shown are always strictly in the order they were entered (even if that means they’re not ordered by actual datapoint date). I’m reluctant to add more visible information in the UI without thinking it all through from the ground up.