Hi and thanks 
I think there are several ways to make this work and it depends on the details of your use case. When you load in your files, do they show up in alphabetical order? (Under the hood, Prodigy calls path.iterdir, which I thought was alphabetic – but turns out that depends on your operating system).
Instead of loading in a directory of images, you could also load in a JSONL file (and set --loader jsonl when you start image.manual). If an image task specifies a "text", that's going to be used in the history pane in the sidebar. So you could use that to give the history entries more readable names, and make sure the files are presented in the right order:
{"image": "group_01/image_01.jpg", "text": "G1: 01"}
{"image": "group_01/image_02.jpg", "text": "G1: 02"}
You can also include other metadata in the tasks – e.g. "group": 1. This will be passed through with the data and saved in the database (and you can later use that to more easily filter your annotations).
One thing to note about the history that it will always show you the 10 most recently edited examples (which makes sense). So if an annotator clicks on an older annotation to change it, it will show up on top, because it was most recently edited. So you couldn't rely on the history always showing the original group order.