We study the synchronization of a Van der Pol self-oscillator with Kerr anharmonicity to an external drive. We demonstrate that the anharmonic, discrete energy spectrum of the quantum oscillator leads to multiple resonances in both phase locking and frequency entrainment not present in the corresponding classical system. Strong driving close to these resonances leads to nonclassical steady-state Wigner distributions. Experimental realizations of these genuine quantum signatures can be implemented with current technology. DOI: 10.1103/PhysRevLett.117.073601 The synchronization of self-oscillators is a subject with great relevance to several natural sciences [1,2]. Its exciting frontiers include neuronal synchronization in the human brain [3,4] and stabilization of power-grid networks [5], as well as the engineering of high-precision clocks [6,7]. Recent advances in nanotechnology will enable experiments with large arrays of self-oscillators in the near future [8,9]. Whereas most research has focused on the classical domain, synchronization in the quantum regime [10] has become a very active topic. There has been much recent experimental progress with micro-and nanomechanical systems [11][12][13][14][15] [29,30].Studying a Van der Pol oscillator, the most prominent example of a self-oscillator, recent theoretical work characterized how synchronization quantitatively differs between its quantum and classical realization in phase locking [24,25] as well as in frequency entrainment [21,22]. While synchronization is hindered by quantum noise compared to the classical model [21,22], noise is less detrimental [24,25] than one would expect from a semiclassical description.In this Letter, we study self-oscillators for which both the damping and the frequency are amplitude dependent. We show that their synchronization behavior is qualitatively different in the quantum and the classical regime. Focusing on a Van der Pol oscillator with Kerr anharmonicity, we find two genuine quantum signatures. First, while the synchronization of one such oscillator to an external drive is maximal at one particular frequency classically, the corresponding quantum system shows a tendency to synchronize at multiple frequencies. Using perturbation theory in the drive strength, we demonstrate that these multiple resonances reflect the quantized anharmonic energy spectrum of the oscillator. We show that these features are observable in the phase probability distribution if the Kerr anharmonicity is large compared to the relaxation rates and the system is in the quantum regime; i.e., the limit cycle amplitudes are small. In the semiclassical limit, the energy spectrum becomes continuous, so that the resonances (and therefore the quantized energy spectrum) cannot be resolved. Using numerically exact simulations of the full quantum master equation, we find a second genuine quantum signature: For strong driving close to these resonances, the steady-state Wigner distribution exhibits areas of negative density; i.e., the steady state is nonclassica...