This paper presents a method for tracking two-dimensional propagation of internal cracks, in particular vertical split head (VSH) defects, due to contact loading in railhead. Generalised curved crack is assumed to have present in the railhead and its propagation is simulated by solving interaction of arbitrary shaped cracks successively. Furthermore, the finite shape of the rail section is also modelled as the continuous distribution of dislocation within an infinite plane. Crack propagation is simulated using the criterion of vanishing of Mode II stress intensity factors (SIF) at crack tips. Examples are provided for tracking the propagation of pre-existing internal cracks in railheads turning into VSH defects under centric contact loading.