Although steel orthotropic deck is currently the most widely adopted solution for long-span bridges, the poor adhesion to the upper asphalt layers still represents a serious problem without a clear solution. In recent decades many techniques that involve the use of special bituminous bonding coats, reinforced asphalt membranes, net-reinforced steel deck surfaces, or epoxy asphalt binders have been applied, with varying results, to improve the level of adhesion of the asphalt pavement to the steel surface. In this experimental study, two such techniques were adopted to investigate the shear resistance of steel–asphalt pavement systems. The first technique used epoxy asphalt both as a bonding coat and as a binder of the upper asphalt layer, while the second technique involved the use of a reinforced asphalt membrane that was applied on the steel deck before overlaying with conventional hot-mix asphalt (HMA). The Ancona Shear Testing Research and Analysis shear test device was used to evaluate the shear resistance of different types of HMA–steel interfaces and to investigate the effects of temperature and normal stress. The results have been compared with the shear properties of bitumen-coated interfaces, studied in previous research. The results showed that epoxy asphalt guaranteed high performance regardless of the test temperature. However, the shear resistance of the system with the asphalt membrane was lower than with the epoxy asphalt, although it was higher than the resistance of bitumen-coated interfaces at high temperatures.