A bicycle shift operating device for operating a shifting device that selectively moves a chain between a first gear having a first diameter and a second gear having a second diameter that is smaller than the first diameter of the first gear using a guiding portion, the bicycle shift operating device comprising: an operating member; a moving member configured to be connected to the shifting device by a connecting member; and a positioning mechanism (78, 80, 82, 84) selectively maintaining the moving member in any one of a first position that locates the guiding portion to a first guiding position where the chain corresponds to the first gear, a second position that locates the guiding portion to a second guiding position where the chain corresponds to the second gear, and a third position that locates the guiding portion to a third guiding position where the chain corresponds to the second gear, the third guiding position being farther from the first guiding position than the second guiding position, the positioning mechanism being configured such that the moving member moves in a first direction from the first position to the second position in response to a single operation of the operating member, the positioning mechanism being void of any position maintaining structure that maintains a position of the moving member between the first position and the second position, wherein the moving member includes a winding member, the positioning mechanism includes a positioning member that rotates with the winding member, and a stopping pawl that engages a stop tooth of the positioning member during rotation of the positioning member in the first direction from the first position to the second position such that the positioning member and the winding member both stop in a position between the first position and the second position. wherein the positioning mechanism further includes a positioning pawl that engages a first positioning tooth of the positioning member while the winding member is in the first position, and that engages a second positioning tooth of the positioning member while the winding member is in the second position, and characterized in that the positioning pawl and the stopping pawl move independently with respect to each other such that the positioning pawl moves between a holding position that is engaged with one of the first and second positioning teeth (78b, 78c) and a non-holding position that is disengaged from the first and second positioning teeth (78b, 78c), and such that the stopping pawl moves between a non-stop position that is disengaged from the stop tooth and a stop position that is engaged with the stop tooth. an operating member; a moving member configured to be connected to the shifting device by a connecting member; and a positioning mechanism (78, 80, 82, 84) selectively maintaining the moving member in any one of a first position that locates the guiding portion to a first guiding position where the chain corresponds to the first gear, a second position that locates the guiding portion to a second guiding position where the chain corresponds to the second gear, and a third position that locates the guiding portion to a third guiding position where the chain corresponds to the second gear, the third guiding position being farther from the first guiding position than the second guiding position, the positioning mechanism being configured such that the moving member moves in a first direction from the first position to the second position in response to a single operation of the operating member, the positioning mechanism being void of any position maintaining structure that maintains a position of the moving member between the first position and the second position, the moving member includes a winding member, the positioning mechanism includes a positioning member that rotates with the winding member, and a stopping pawl that engages a stop tooth of the positioning member during rotation of the positioning member in the first direction from the first position to the second position such that the positioning member and the winding member both stop in a position between the first position and the second position.