Asymmetric functionalization of alkenes is a powerful transformation to access a variety of chiral molecules. This chapter discusses strategies for the reagent-controlled enantioselective chloro-, bromo-, or iodofunctionalization of alkene substrates. The resulting products from the vicinal stereoselective halofunctionalization of alkenes provide access to chiral heterocycles, synthetic building blocks, and key intermediates for the syntheses of natural products. A historical perspective with regards to both reaction development as well as the numerous mechanistic challenges for this class of transformations are discussed. The accompanying tables are a glossary of reactions that are organized by the halogen electrophile and further classified by the identity of the nucleophile. Representative protocols as well as application of asymmetric alkene halofunctionalization in kinetic resolutions, desymmetrizations, and total synthesis are also presented.