I lost what was probably 100 or so points on my SAT because I think someone messed up the papers.
There was a section which began with question numbers in the 30s. Knowing that not everyone is given the same copy of the test (to deter cheating), I didn't think anything of it, and just started with #30 on the bubble sheet for that section. Now, I am not someone who ever leaves questions unanswered, so when it came back that I hadn't answered 20-odd questions I knew what had happened, but I was 0% assertive at that time so I just never said anything to anyone.
It was a decent share of the math section so I'm sure it cost me at least 100 points. Might have benefited me with paying for school, and I might have actually finished, if not for that. Ah well.