A rolling cone for use on an earth-boring tool includes a frustoconical surface at a proximal end of the rolling cone and an outer surface located distally of the frustoconical surface. The outer surface has a circumferential land surface adjacent the frustoconical surface. The rolling cone includes at least one gage cutting element affixed to the circumferential land surface. A portion of the at least one gage cutting element extends into the frustoconical surface. The at least one gage cutting element includes a volume of superabrasive material disposed on a substrate. A flat surface of the volume of superabrasive material intersects a front cutting face of the volume of superabrasive material. The flat surface is oriented at an acute angle relative to the front cutting face and is located on a side of the at least one gage cutting element that extends into the frustoconical surface of the rolling cone.