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I don't use Steam. But I also use the historical matchup feature often and I understand your frustration. What I do is, after I set up the matchup and rosters, I then exit to the OOTP Main Menu. You should be able to do that by clicking on it at the top right hand corner of the rosters page.
Now it will be among your saved game as "historical matchup", you can load it just like any other game and then you can play the games out and customize lineups and stadiums like you would for any full game load or season.
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