This paper presents an experimental study on ductility and overstrength of dowelled connections. Connection ductility and overstrength derived from monotonic testing are often used in timber connection design in the context of seismic loading, based on the assumption that these properties are similar under monotonic and cyclic loading. This assumption could possibly lead to non-conservative connection design. Therefore, it is necessary to quantify ductility and overstrength for cyclic loading and contrast them with their monotonic performance. For this purpose, monotonic and quasi-static cyclic experimental tests were performed on dowelled LVL and CLT connections. The experimental results were also compared with strength predictions from state-of-the-art analytical models in literature that were verified for ductile and brittle failure under monotonic loading. This work also allowed investigation into a generally applicable overstrength factor for push-pull loaded dowelled connections.