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33,
33, from Italy
Elder
If I'm not mistaken, I think the flag preceding the current Italian one is the flag of the Italian Social Republic
https://it.wikipedia.org/wiki/File:War_flag_of_the_Italian_Social_Republic.svg
15,
15, from Finland
Casual

Im quite sure for finland its "leijona lippu". Used in 1917 after independence and 1920 it was abandoned.
27,
27, from Croatia
Explorer
https://en.wikipedia.org/wiki/Flag_of_Croatia#/media/File:Flag_of_Croatia_(1990).svg/2 I think this one was for Croatia, it's from 1990 shortly before the last war. Only difference is absence of a crown above the coat of arms
99,
99, from United States
Explorer
49‐state US flag:

A more varied pre‐US flag:
