The lists almost always consist primarily of biblical history – the creation of the world, the flood, exodus from Egypt, etc. After noting the destruction of the second temple, the Ashkenazic calendars (published in Metz, Berlin, Sulzbach, and Frankfurt am Main) jump directly the dates of the expulsion of Jews from various locales. No history of the rabbinic period or the Middle Ages. That’s it. Jewish history in a nutshell.
The Sephardic lists diverge slightly. Medieval Jewish history in these lists centers on one important person: the Rambam. They note when he was born and died, and maybe when he authored the Mishneh Torah. They too then list the expulsions of Jews, and the English ones end with the foundation of the New Synagogue (or Bevis Marks Synagogue).
These lists remind me of Yerushalmi’s argument in Zakhor, although to my recollection he does not use these calendars. Jewish history in these lists is a strange amalgam of sacred history and actual history, the creation of usable Jewish memory that one can carry in a pocket.