An object of the present invention is to provide a winding switching device capable of enhancing the reliability of electrical contact between a movable unit and a fixed unit, and a rotating electrical machine drive system including such a winding switching device. A winding switching device switches a connection state of a plurality of windings, and includes a plurality of electrodes to which the plurality of windings are connected; a movable unit that includes a plurality of conductor portions in contact with the plurality of electrodes, and that is driven in a predetermined direction in which the plurality of electrodes are arranged; and a fixed unit including a regulating portion that regulates movement of the movable unit in the predetermined direction; where the connection states of the plurality of windings are switched according to the position of the movable unit; and when the movable unit moves in the predetermined direction, the plurality of conductors are displaced in a direction of moving away from the plurality of electrodes by the regulating portion.