This paper aims to evaluate the surface cracking phenomenon on a flexible pavement subjected to diverse vehicle running conditions. Top-down cracking initiation is addressed through a continuum damage framework coupled with a semi-analytical model of tire-pavement rolling contact. The acceleration, braking and cornering scenarios were selected to represent the effect of combining normal and tangential loads. The differences between these loading cases are accurately computed by simulating the realistic contact stresses on the pavement surface through semi-analytical modelling. The computational cost of this modelling technique is reduced, allowing it to be used in industrial applications. It is assumed that tires and pavement are linear elastic multilayered half-spaces. The critical locations of the cracks are identified for each loading scenario and the cracking directions are discussed. This study emphasises the influence of driving conditions on premature pavement cracking which is not typically considered in the current pavement design guides. It is shown that a standard axle load may cause about 9 times more surface damage on a circular intersection compared to a straight-line pavement section.