Fretting tests were conducted with five different thermoplastic polyurethanes against a steel ball. Their fretting behaviors were investigated under various test parameters, such as normal load and displacement amplitude. In order to test the sliding performances, tribological tests were conducted using a ring-on-disc setup. The results show that their fretting behaviors can be related to the dynamic mechanical properties, which were characterized by dynamic mechanical analysis (DMA). The three fretting regimes were identified by means of hysteresis and wear scar analysis. In addition, investigations were carried out until the transition regimes occurred. Different wear processes were revealed for each of the three regimes. Differences were identified using dissipated energy. The profiles of wear scars and the counterparts were analyzed using a microscope. The coefficient of friction was calculated separately for the partial slip and gross slip regimes. In the mixed fretting regime, the coefficient of friction is almost at the same level among the five materials. In the partial slip regime, however, it can be distinguished. Temperature measurements were conducted on the counterparts during the tests. Overall, the material that showed the best tribological properties also performed the best in the fretting tests.