Rolling Autosaves (or at least Multiple Saves)
 

Ootp20 was/is great, and this series has come a long way from when I first played it in 2012. Yet the game still lacks an ability to have multiple save files for the same career, which has cost me about six seasons of work due to my files becoming corrupted. I know there is a backup feature, but I do not think it is a sufficient replacement for being able to make multiple saves, or even better to have rolling autosaves.
I want to keep playing but every time I go to go back I remember my career is gone and I lose motivation - I would be thrilled if I did not have to worry about this possibility in future versions. Thanks for all the work you do

I'm not sure that would be a heavily used feature since I can't think of another game I've played that has "rolling autosaves," but I could be wrong.

The simple solution right now is each time you're done playing, go into the folder where your saved game is stored and copy that folder to another folder on your hard drive, onto a cloud drive or an external hard drive. Label the folder with a date or keep track somehow of the date, and then you'd just have to copy that folder back into your saved games folder if you want to revert to that point in your game. Just remember that if you don't change the name of that duplicate folder, it'll copy over the current version of your saved game.

Agree with this, but for different reasons,

I like to do a lot of "what ifs". So, play out one reality, then go back to a certain spot and play out another.

The most obvious example comes from across the pond - Football Manager, the other biggest sports text sim.

This is actually present in a lot of games.

Never played it. I can see its usefulness, but having been around these parts for 10 years and never seeing someone ask for this until now, that's what leads me to believe it wouldn't be a heavily used feature. But I could be wrong.