An energy-controlled cycling impact test was applied to evaluate the impact wear behavior of hard coating. A multilayer TiN/Ti coating with a total thickness of ~10 μm, containing two TiN layers and two Ti layers, with the thickness ratio of these two kinds of the layers being 9:1, was chosen as the research object. The impact velocities were 60, 120, and 180 mm/s, and the impact cycles were 10, 102, 103, and 104, respectively. Damage morphology observation and numerical simulation were used to analyze the failure mechanisms. The results show that the contact time keeps almost constant under different impact velocities and cycles. Impact peak forces remain unchanged with increasing cycles at the same velocity, but they increase linearly with impact velocities, reaching a maximum value of 262.26 N at 180 mm/s. The energy dissipated rate (EDR) increases from 31.58% at 60 mm/s to 35.59% at 180 mm/s, indicating the degenerative toughness. Two impact-wear failure mechanisms are found in impact zones of the coating; these are peeling and circular cracks. Peelings are induced by cycling high-stress gradients in hard layers and interfaces. Circular cracks are caused by cycling tensile stresses in the form of fatigue at the edge of impacted pits.