I've read Caesar's Gallic War (Commentarii de Bello Gallico) and Civil War (Commentarii de Bello Civili) probably ~300 times but I don't have an exact count. They're relatively short texts.

I've re-read them non-stop for ~20 years any time I don't have something else I'm excited to read. I discovered them as a teenager but still find them fascinating. I find new things to think about every time I read them.