Never
I think it unlikely, in game or real life, that one lone U-Boat could do anything that could seriously change the war outcome.
Just consider the number of ships involved in D-Day. You have a limited supply of torps and are outnumbered by the destroyers alone!
If the Bismarck has survived, it would have caused some damage, but it too could not face the British fleet alone. It was sent out alone! It is fitting that its end was by airpower, a portent of the future.
If it had sunk 1-4 British battleships or cruisers, there were lots left. Even a sub might have caught it somewhere. When damaged, it would have to find a hole, like Graf Spee did. A long way from home and no friends.
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