A bicycle shift operating device comprises a bicycle mounting member, a shift operating member, a take-up member, a positioning member, a first retaining mechanism and a second retaining mechanism. The shift operating member is rotatably coupled to the mounting member to move in opposing rotational directions. The take-up member is rotatably coupled to the mounting member to selectively pull and release a shift control cable. The positioning member is rotatably coupled to the mounting member. The first retaining mechanism is arranged to retain the positioning member relative to the mounting member. The second retaining mechanism is coupled to the take-up member and the positioning member to normally apply a retaining force on the take-up member and the positioning member. The second retaining mechanism is arranged to reduce the retaining force upon moving the shift operating member.