This paper presents an experimental study on dowelled connections in Cross Laminated Timber (CLT) and Laminated Veneer Lumber (LVL) using ϕ20 mm mild steel dowels and internal steel plates. Connections designed to fail in brittle row shear and group tear-out were tested under monotonic loading to assess the validity of analytical models from literature and code provisions. Connections designed to provide non-linearity before failure and thus produce ductility were tested under both monotonic and cyclic loading to study the influence of cyclic loading onductility and the possibility of mode cross-over. It was found that cross layers in CLT improveductility. Furthermore, mode cross-over from ductile response to brittle failure was observed inboth CLT and LVL connections. Nevertheless, a good amount of ductility was achieved in all layouts (except the LVL connections designed for group tear-out failure) before cross-over to brittle failure occurred.