Chiral allenes and styrenes are essential components in fields like medicinal chemistry, materials science, and organic synthesis. They serve a crucial role as chiral ligands and catalysts in asymmetric synthesis. Over the past decade, there has been a significant advancement in the development of practical methods utilizing organocatalytic strategies for the synthesis of chiral allenes and styrenes. It is noteworthy that despite extensive studies on the formation of allenes and styrenes, existing reviews on their construction confined to a specific organocatalysis, called chiral phosphoric acid catalysis, are less documented. This review aims to explore different conceptual approaches based on the electrophilic species involved in the reaction to produce stereoselective chiral allenes and styrenes, providing insights into recent advancements in the field. Emphasis is placed on works published since 2017, with detailed discussions on reaction mechanisms and examples from recent literature.