I believe OOTP 10 was the first version with real players, there were only a few though... Stephen Strasburg and his 2009 counterparts...
I have to say though, I would really like to see something like this happen, where would could pick a past OOTP quickstart and play it in the most updated version of OOTP. The earliest version of OOTP I can play on my laptop is OOTP 12, but OOTP 11 was my first version and it was always fun going to back the grassroots and playing a little bit.
I support this idea and I'm sure many others do as well!
Where y'all at?