Prior to becoming a state, Hawaii was a territory after the illegal coup of its monarch. This occurred in 1900, and to the best of my knowledge, citizens of territories were US citizens in all respects (setting aside all the racist bits of the history of US citizenship), so even in the specific example, there would not be a question of citizenship.
Specifically, the organic act that annexed Hawaii states:
SEC. 4. That all persons who were citizens of the Republic of
Hawaii on August twelfth, eighteen hundred and ninety-eight, are
hereby declared to be citizens of the United States and citizens of the
Territory of Hawaii.
This does not seem to confer retroactive birthright citizenship, but I'm not a lawyer. The act granting Hawaii statehood does not mention citizenship.
For comparison, the Jones Act that annexed Puerto Rico explicitly does not grant retroactive citizenship (emphasis added):
All persons born in Puerto Rico on or after April 11, 1899, and prior to January 13, 1941, subject to the jurisdiction of the United States, residing on January 13, 1941, in Puerto Rico or another territory over which the United States exercises rights of sovereignty and not citizens of the United States under any other Act, are declared to be citizens of the United States as of January 13, 1941. All persons born in Puerto Rico on or after January 13, 1941, and subject to the jurisdiction of the United States, are citizens of the United States at birth.
So in conclusion, if you were born before the annexation of a territory, you were probably not granted retroactive birthright citizenship habitually, although it might depend on the specific act annexing a territory. It would not surprise me if some act granted birthright citizenship for some political reason.