I have two errors (more spell check than auto-correct) that have stuck in my mind for a long time.
During my A Levels (I was 18), I was late handing in an Economics essay about regulation of the Bank of England, so I wrote it one night with the computer in front of the TV, watching a soccer game. At the time, the Chairman of the Bank of England was Eddie George. Throughout the whole essay, I referred to him as "George Graham" - the manager of one of the teams playing. It highly amused my teacher.
At work, (as a Legal Secretary), I was transcribing a letter about a person who had suffered a serious brain injury in a workplace accident and, hence, was unable to handle his own affairs. Fortunately, I caught the error as I was putting the (signed) letter into an envelope - I had mistyped and instead of "Kind regards" I had typed "King retards". I'm so glad I caught that one!