A new numerical model is presented to simulate fracture initiation and propagation in geological structures. This model is based on the recent amalgamation of established failure and fracture mechanics theory, which has been implemented to the finite difference FLAC code as a constitutive FISH userdefined-model. Validation of the model has been studied on the basis of comparing the transitional failure modes in rock. It is shown that the model is capable of accurately simulating fracture distributions over entire brittle to ductile rock phases. The application of the model during longwall retreat simulation highlighted several caving characteristics relevant to varying geological condition. The distribution and behaviour of modelled fractures were both realistic and shown to provide an enhanced post failure analysis to geological structures in FLAC. Moreover, the model introduces new potential insight towards the failure analysis of more complicated problems. This is best suited towards improving safety and efficiency in mines through the prediction of various key fractures and caving characteristics of geological structures. A new numerical model is presented to simulate fracture initiation and propagation in geological structures. This model is based on the recent amalgamation of established failure and fracture mechanics theory, which has been implemented to the finite difference FLAC code as a constitutive FISH user defined-model. Validation of the model has been studied on the basis of comparing the transitional failure modes in rock. It is shown that the model is capable of accurately simulating fracture distributions over entire brittle to ductile rock phases. The application of the model during longwall retreat simulation. The distribution and behavior of modelled fractures were both both realistic and shown to provide an enhanced post failure analysis to geological structures in FLAC. Moreover, the model introduces new potential insight towards the failure analysis of more complicated problems This is best suited toward s improving safety and efficiency in mines through the prediction of various key fractures and caving characteristics of geological structures.