Accurate modelling of the potential failure modes in the rock mass is an essential task towards a robust design of roof support systems in coal mines. The use of generalised rock mass properties based on averaged properties (e.g. Hoek-Brown model) has been found to limit the capability to reproduce the actual rock mass behaviour which may include a wide range of interacting and complex failure mechanisms such as shear and tension fracturing of the intact rock and shear and separation of pre-existing discontinuities, including re-activation. Recent studies have also shown that traditional models, such as the Mohr-Coulomb, may not accurately describe the behaviour of the intact rock, particularly for stress induced failures where spalling and slabbing are observed. This is mainly due to the cohesion and friction components of the shear strength of the intact rock not being mobilised at the same rate with strain-softening of the former component playing an essential role in the post peak behaviour. In addition, coal measure rocks are often transversely isotropic, both by way of the preferred orientation of clay particles within the finer grained lithology and by bedding textures and bedding partings, and this is often ignored in computer simulations. A newly developed transversely isotropic brittle rock mass model is applied in the simulation of a hypothetical and simple roadway development. A Cohesion Weakening - Friction Strengthening (CWFS) approach is adopted to describe the intact rock where the mobilisation and strain-softening of the two shear strength components are linked to plastic deformation. Failure and plastic deformations are also allowed to develop along any number of ubiquitous joint sets using a conventional Mohr-Coulomb failure criterion and applying the stress-strain correction accordingly. The impacts of anisotropy and brittle rock on the development of the excavation disturbed zone or height of softening, as often referred to, are investigated and their implication in the roof support design discussed.