The application of fracture mechanics to predict the cracking damage in masonry buildings subjected to ground movement by tunnelling activity is presented in this paper. It describes the computational approach employed to capture the failure mechanism of a selected historical masonry façade. Both uncoupled and coupled soil-structure analyses are performed. Various continuum crack models are tested in large-scale fracture analyses. The results indicate the need for reliable numerical techniques for large-scale fracture analysis of highly brittle material.