The current study examined the plain fatigue and the fretting fatigue behaviors of the piston pin alloy (16MnCr5 steel) under fully-reversed rotating bending loading. The standard fatigue testing sample was cut out from the piston pin used in internal combustion engines. Furthermore, the failure mechanisms of samples were studied using field emission scanning electron microscopy. The obtained result indicated that the fatigue lifetime of 16MnCr5 steel was significantly affected by the fretting damage. The investigation of the failure mechanisms determined that the fracture behavior of the specimens under the plain fatigue and fretting fatigue conditions was brittle; however, it was considerably influenced by the casting defects in the samples. The test results can merely be used to compare the fatigue performance of the studied material under different conditions. More naturalistic experiments are required for further optimization in designing components made from this material to improve their reliability and service life, especially in contacting surfaces under rotating bending conditions.