Text on the front of the cup reads: 凱隊紀念 "Commemorating the victorious unit" 

Text on the bottom rim reads: 歩兵第九聯隊 "9th Infantry Regiment" 

Given the old form of 紀 vs 記 this is probably Meiji/Taisho era. The 9th Infantry Regiment fought in the Russo-Japanese War and the 1st and 2nd Sino-Japanese wars, given the victory celebration terminology this cup is likely from one of those 3 wars.