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This has been a problem since I started playing OOTP 5. It is a major problem in pre1900 historical leagues where you have 1-3 pitchers and rosters as small as 11 players. The only way to catch and fix this problem is to manage both teams for every game so you can fix the lineup, start the game then you can go back to the computer manager.
There seems to be a disconnect between the depth chart and the pitching rotation. What I would suggest is the the pitcher be selected first and that player is flagged as unavailable for the depth chart which is then filled with the next available player.
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