Group Interaction Modelling has been extended to predict a range of thermo-mechanical properties of diglycidyl ether of bisphenol A cured with two isomers of diaminodiphenyl sulphone. The meta-meta and para-para positions of the substituents on the phenylene rings in the curing agent cause differences in packing efficiency, reaction kinetics and conformational freedom. Experimental data in the form of dynamic mechanical, static mechanical and density measurements are acquired in order to provide validation for the model. The model has proven capable of accurately reproducing the experimental measurements to well within experimental errors in most cases. Both the experimental measurements and model predictions have highlighted a number of subtle differences in behaviour of the resins cured with the two diamine isomers. In particular, variation of the amine/epoxy ratio has revealed how the secondary phase transitions of the resins are influenced. Variation of the glass and beta transitions in amine rich, stoichiometric or epoxy rich mixtures is described in terms of the molecular motions responsible for the transitions and the underlying network structural differences between the meta and para isomers.