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As a significant complement to amino catalysts, phosphines are versatile Lewis base catalysts capable of promoting a wide range of diverse organic transformations. In particular, chiral phosphines bearing a Brønsted acid moiety have recently emerged as powerful bifunctional phosphine catalysts in asymmetric synthesis and catalysis. In this account, we document our recent efforts on the design and development of novel amino acid/dipeptide-based bifunctional chiral phosphines, and their applications in enantioselective (aza)-Morita-Baylis-Hillman (MBH) reactions and [3+2]-cycloaddition reactions.