Top text reads 歩二九 "29th infantry" likely 29th infantry regiment. Text below that reads 除隊紀念 "commemorating completing service" this is standard honorable discharge terminology. Bottom text reads 松 野 "Matsuno" this is the surname of the soldier who was issued this cup. The central imagery shows a Type 11 Light Machine Gun. Based on that and the design of the foot of the cup I think it's safe to assume the cup dates from around the 1920s