The last official Jubilee was when Tribes dwelt according to their territory, probably around the First Exile. Maimonides’ calculations would indicate the last Jubilee would have been celebrated 2004/5.
Christianity, being a different religion, can calculate it however it wishes, although such would have no impact on Jewish practice.
Messiah is the same regardless of what ‘religion’ is at issue. He came as a suffering servant the first time. The soon return He will come as the conquering King.