how old are these bullet casings?

[ATpro5]

Some stamped with a large U and some with a large H. I'm guessing they are from henry arms and the union metallic cartridge co.

 

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[ATpro5]

 

[Charlie P. (NY)]

"H" are Winchester and "U" are Remington/UMC if they are .22LR cases (appear to be - need measurements). 1890's to 1990's.