A bicycle operating device operates a bicycle component by moving a winding member that moves a take-up member relative to a fixed member in first and second directions. A positioning member is movably arranged with respect to the fixed member between a non-holding position and a holding position to selectively engage a positioning ratchet that is fixed to the take-up member. In the holding position, the positioning member prevents the take-up member from moving in the second direction by selectively engaging one of at least three engaging portions of the positioning ratchet. A preventing member is movably arranged with respect to the positioning ratchet such that the preventing member prevents the positioning member from engaging an intermediate engaging portion of the positioning ratchet while the winding member moves the take-up member in the first direction.