A tapered roller bearing includes an inner ring, an outer ring, a plurality of tapered rollers provided between the inner ring and the outer ring, and an annular cage. The cage has a small-diameter annular portion on a first side in an axial direction, a large-diameter annular portion on a second side in an axial direction, and a plurality of cage bar portions. The cage has pockets that are spaces each formed between the large-diameter annular portion and the small-diameter annular portion and between the adjacent cage bar portions in a circumferential direction and in which the tapered rollers are held. The cage further has a roller retaining portion that inhibits the tapered rollers housed in the pockets from falling outward in a radial direction. A recessed portion is formed in the small-diameter annular portion to reduce rigidity of the small-diameter annular portion.