The main purpose of this study is to determine the effect of overlay on the crack propagation. In order to simplify the problem, a cement concrete pavement is modeled as an elastic plate on Winkler foundation. To derive the singular integral equations, the Fourier transform and dislocation density function are used. Lobatto-Chebyshev integration formula, as a numerical method, is used to solve the singular integral equations. The numerical solution of stress intensity factor at the crack tip is derived. In order to examine the effect of overlay for resisting crack propagation, numerical analyses are carried out for a cement concrete pavement with an embedded crack and a concrete pavement with an asphalt overlay. Results show the significant factors that influence the crack propagation.