The asphalt overlay is a major maintenance strategy to improve the performance of cracked pavement. However, the crack would propagate upwards and eventually reach to the limit of service life. The potential of the crack propagation of overlaid pavement with cracks will be the key point to evaluate the overlay strategy and the pavement service life. In this study, the Extended Finite Element Method (XFEM) in ANSYS was utilized as the analysis engine to establish the pavement finite model with cracks. Taking Beijing area as example, the transient thermal analysis module was used to construct the 24-hour temperature field in winter. The stress intensity factor (SIF) was adopted as the index to evaluate the effectiveness of the overlay thickness, the length and inclination of crack, as well as temperature under traffic loading. The results indicated that the sliding crack is the major fracture mode for pavement under pure vehicle loading, while the mixed mode of opening and sliding mode changes to be the major fracture mode for pavement under low temperature. The geometric property of existing crack has a significant influence on the critical loading position and peak value of SIF in overlaid pavement. And the promotion effect of increasing the overlay thickness on preventing crack propagation was gradually weakening. The achievement in this study will bring an insight into crack propagation for pavement overlay paving as well as the pavement maintenance.