Provided is a tapered roller bearing (1) subjected to a thrust load and a radial load from a rotation axis (JX). The tapered roller bearing (1) comprises: a plurality of rollers (50) arranged radially between a pair of raceway surfaces (2a, 3a) tilted to one side relative to a plane (P1) perpendicular to the rotation axis (JX); and a retainer (4) disposed between the pair of raceway surfaces (2a, 3a) and having a plurality of pockets (41) for containing the rollers (50). Each of the rollers (50) has: a truncated circular conical roller body (51) having a diameter gradually increasing from the inner side toward the outer side in a radial direction (DD); and a circular conical roller outer section (52) continuous with the outer side of the roller body (51) in the radial direction (DD) and tapered toward the outer side in the radial direction (DD). The inner sides of the rollers (50) in the radial direction (DD) are shaped to conform to the shape of the inner walls of the pockets (41) and are not rotatably supported by the pockets (41), and the outer sides of the rollers (50) in the radial direction (DD) are in point-contact with the inner walls of the pockets (41).