Tomorrow is Yesterday - S1-E20
Factual error: Towards the end of the show the Enterprise is leaving Earth orbit and heading towards the sun. We see the Earth diminish and the moon appear looking exactly as it does from Earth. From this angle we should be seeing the "dark side" of the moon, which looks completely different. (00:40:50)
Factual error: When Ulysses opens his mouth while speaking, modern dental fillings are in his teeth.