In this study, the adhesion properties of polyurethane (PUR) pressure-sensitive adhesive (PSA) were investigated. The PUR-PSA was prepared by the cross-linking reaction of a urethane polymer consisting of toluene-2,4-diisocyanate and poly(propylene glycol) components using polyisocyanate as a cross-linking agent. The peel strength increased with the cross-linking agent content and exhibited cohesive failure until the maximum value, after which it decreased with interfacial failure. The PUR-PSA exhibited frequency dependence of the storage modulus obtained from dynamic viscoelastic measurements, but did not show dependence of the tack on the rolling rate measured using a rolling cylinder tack test under the experimental conditions used, which is quite different from the acrylic block copolymer/tackifier system. The PUR-PSA showed strong contact time dependence of tack measured by a probe tack test. The tendency was significantly larger than for the acrylic block copolymer/tackifier system. Therefore, the storage modulus increased, whereas the interfacial adhesion seems to be decreased with increase in the rolling rate for this PUR-PSA system. It was estimated that the influence of rolling rate on the interfacial adhesion and the storage modulus was offset, and, as a result, the rolling cylinder tack did not exhibit rate dependency.