Enyne cycloisomerizations can provide an efficient means for forming carbon-carbon bonds. We describe stereoselectively dichotomous enyne cycloisomerizations, entirely dependent on the selection of catalytic manifold. Ruthenium catalysis provides transfused bicyclic systems, whereas palladium catalysis provides the analogous cis-fused bicycles. A number of substrates are investigated, and the outcomes ultimately offer a clear mechanistic rationale for these observations,