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Bottom interior text reads as 輜重九 "9th Transport/Supply Corps"
Top interior text reads as 除隊記念 "Discharge from military service commemoration"
The outside of the cup shows a fighter plane, a tank, a battleship, an LMG and a giant crab eating a ship. This is the reference to the WW2 Japanese legend of giant crabs eating soldiers. This is a very unique design for an imperial Japanese commemorative cup.
The text on the outside of the cup above the LMG is very hard to read. It appears to include 日米, 日米 being "Japan-America" and is commonly used in WW2 phrases. 対米日戦 being "War against America".