A web winding apparatus comprises two bobbins each being able to wind a web thereon; a cutter provided movably between the bobbin on one side and the bobbin on the other side for cutting the web being transferred; and a web pressing member provided at a position to face the cutter so that the web being transferred is put between the web pressing member and the cutter. The web pressing member is provided movably together with the cutter between the two bobbins, is configured to operate as cutter receiving member which presses and cuts the web in cooperation with the cutter, and is further configured to press a cut end of the web so cut on the bobbin being empty while holding the cut end of the web, to wind the cut end on the bobbin being empty.