Lubricant draining bearing assemblies are disclosed. An example apparatus includes a first race, a second race, roller bearings positioned between the first race and the second race, and a cage positioned around the roller bearings between the first race and the second race, the cage including a first radial surface, a second radial surface, and an axial surface, the first radial surface facing the first race, the second radial surface facing the second race, the axial surface facing away from the roller bearings, the cage including at least one conduit extending between the first radial surface and at least one of the second radial surface or the axial surface, the conduit defining a flow path for a fluid out of a cavity between the first race, the roller bearings, and the cage.