With the use of experimental wood properties and input moisture content field data, a predictive 3D stress–strain finite element analysis (FEA) model was developed allowing to predict the development of stress-related end splitting and surface checking degrade during conventional and vacuum wood drying. Simulations were carried out for two Australian hardwood species, messmate (Eucalyptus obliqua) and spotted gum (Corymbia citriodora), as these species contrast, in terms of wood properties, drying rates and stress degrade susceptibility. The simulations were performed using a 1/8 symmetry model where the full board dimensions are 1900 mm long × 30 mm thick × 100 mm wide. Moisture content field data model simulations were utilised in a three-dimensional FEA model by extruding a 2D moisture content field computed in the T–L plane across the radial direction to create a 3D model. Material mechanical properties and shrinkage were calculated in relation to moisture content, over discrete time intervals, using a quasi-static solver. End split failure was investigated at the board end, and surface check failure at the board surface, using a Tsai–Wu failure criterion. Simulations showed that messmate was more susceptible to end splitting than spotted gum and that conventionally dried messmate was more susceptible to surface checking than vacuum-dried messmate. The same results were observed from drying trials. The locations of predicted surface check failure also matched drying trials and are compared.