A boundary element method is applied to the analysis of crack trajectory in materials with complex microstructure, such as discontinuously reinforced composite materials, and systems subjected to complex loading, such as indentation. The path followed by the crack(s) has non-trivial geometry. A study of the stress intensity factors and fracture toughness of such systems must therefore be accompanied by an analysis of crack trajectory. The simulation is achieved using a dual boundary integral method in planar problems, and a single boundary integral method coupled with substructuring in axisymmetric problems. The direction of crack propagation is determined using the maximum mechanical energy release rate criterion. The method is demonstrated by application to (i) a composite material composed of components having the elastic properties of aluminium (matrix) and silicon carbide (reinforcement), and (ii) analysis of contact damage induced by the action of an indenter on brittle materials. The chief advantage of the method is the ease with which problems having complex geometry or loading (giving rise to complex crack trajectories) can be treated.