A bicycle shift operating device is basically provided with a first operating member, a second operating member, a shift wire take-up element and a wire winding/release mechanism. The second operating member is operatively coupled to the first operating member to move with the first operating member during movement of the first operating member, and to move the first operating member during movement of the second operating member. The shift wire take-up element is rotated in a first rotational direction by the first operating member and in a second rotational direction that is opposite to the first rotational direction by the second operating member. The wire winding/release mechanism is operatively coupled to the shift wire take-up element and the first and second operating members to selectively hold the shift wire take-up element in one of a plurality of shift positions.