A tapered roller bearing includes a retainer formed with a plurality of trapezoidal pockets. Each pocket includes cutouts formed in the crossbars defining each pocket near the narrow end thereof. A tapered roller is received in each pocket with its small-diameter end facing the narrow end of the pocket. Lubricating oil flowing into the bearing space defined radially inwardly of the retainer can quickly flows through the cutouts into the bearing space defined radially outwardly of the retainer at the narrow end of each pocket. Thus, it is possible to reduce the amount of lubricating oil flowing along the raceway of the inner ring to the large-diameter flange, and thus reduce the amount of lubricating oil remaining in the bearing, thereby reducing the torque loss due to rotational resistance of the bearing resulting from lubricating oil remaining in the bearing.