Olefin metathesis has been one of the most important methods to construct carbon-carbon double bonds, which has been catalyzed by ruthenium carbene. Investigations in olefin metathesis have focused on stereoselective transformations in recent years. The research progress on the applications of stereoselective olefin metathesis reactions catalyzed by ruthenium carbene complexes is reviewed. The advancements in stereoselectivity of olefin metathesis are described in detail, and the categories and improvement of ruthenium catalysts are also introduced over the past decade. Finally, the future development for olefin metathesis is further evaluated as well.