Of course it doesn't know how. But it knows the number. And I don't. If I would know what the time machine knows, the number of lost drillers, I could speculate. If there is a sudden drop of exactly 100 drillers and the player has 1 mine it is pretty sure he drills a mine.
I just thought it would be right to have every information the time machine can provide. Either the player should see the statistics for any given time as the time machine calculates them, or the time machine shouldn't consider future losses that are out of my range.
Edit: This doesn't only include number of drillers but everything the statistics tab show. For example the current production rate. I can skip forward and see who will win when everything stays the same. But I can't see the exact rate of neptunium production. I am currently in a very close game. I am second with 1 mine, first player has two, but I have more outposts. I am going to take a mine from a third player which should raise my production over that of the first player. The game still says he will win, this means I catch up, but not fast enough. If I could see the statistics of any given time I would know exactly how close it will be. I know I could do the math by myself, but the time machine knows all the numbers. It could just tell me.