Within the framework of the piecewise homogeneous body model the influence of the shear-spring type imperfect contact conditions on the dispersion relation of the generalized Rayleigh waves in the system consisting of the initially stressed covering layer and initially stressed half plane is investigated. The second version of the small initial deformation theory of the three-dimensional linearized theory of elastic waves in initially stressed bodies is applied and the elasticity relations of the materials of the constituents are described by the Murnaghan potential. The magnitude of the imperfectness of the contact conditions is estimated through the shear-spring type parameter. Consequently, the influence of the imperfectness of the contact conditions on the generalized Rayleigh wave propagation velocity is studied through the influence of the values of this parameter. Numerical results on the action of the imperfectness of the contact conditions and the influence of the initial stresses in the constituents on the wave dispersion curves are presented and discussed. In particular, it is established that the magnitude of action of the imperfectness of the contact conditions under the influence of the initial stresses on the wave propagation velocity cannot be limited with corresponding ones obtained in the case where the contact between the constituents is complete and in the case where this contact is full slipping one. The possible application of the obtained results on the geophysical and geotechnical engineering is also discussed.