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Viscoelasticity is well known to cause significant hysteresis of crack closure and opening when an elastomer is brought in and out of contact with a flat, rigid, adhesive counterface. A separate origin of adhesive hysteresis is small-scale, elastic multistability. Here, we study a system in which both mechanisms act concurrently. Specifically, we compare the simulated and experimentally measured time evolution of the interfacial force and the real contact area between a soft elastomer and a rigid, flat punch, to which small-scale, single-sinusoidal roughness is added. To this end, we further the Green's function molecular dynamics method and extend recently developed imaging techniques to elucidate the rate- and preload-dependence of the pull-off process. Our results reveal that hysteresis is much enhanced when the saddle points of the topography come into contact, which, however, is impeded by viscoelastic forces and may require sufficiently large preloads. A similar coaction of viscous- and multistability effects is expected to occur in macroscopic polymer contacts and to be relevant, e.g., for pressure-sensitive adhesives and modern adhesive gripping devices.