The current study investigates the influence of timber-to-concrete connection types on the behaviour of timber–concrete composite (TCC) structures employing metal web timber joists. Two groups of laboratory specimens were prepared, each comprising four samples with push-joisted beams joined by oriented strand board (OSB) and cast with a concrete layer. One group utilised compliant timber-to-concrete connections via perforated steel tape angles, while the other employed rigid connections through epoxy adhesive and granite chips. The specimens, consisting of two 1390 mm long beams of grade PS10 timber, were tested under three-point bending. Experimental results and finite element analyses demonstrated that specimens with compliant connections exhibited 14–16% greater maximum vertical displacements but only a marginal 1.79% reduction in load-carrying capacity compared to those with rigid connections. Findings indicate that connection compliance markedly affects stiffness and deflection but has a minor impact on ultimate strength. These insights can guide optimisation of TCC members with metal web joists, balancing structural performance and design requirements in sustainable timber construction.