Linear and nonlinear fractional-delay systems are studied. As an application, we derive the controllability and Hyers–Ulam stability results using the representation of solutions of these systems with the help of their delayed Mittag–Leffler matrix functions. We provide some sufficient and necessary conditions for the controllability of linear fractional-delay systems by introducing a fractional delay Gramian matrix. Furthermore, we establish some sufficient conditions of controllability and Hyers–Ulam stability of nonlinear fractional-delay systems by applying Krasnoselskii’s fixed-point theorem. Our results improve, extend, and complement some existing ones. Finally, numerical examples of linear and nonlinear fractional-delay systems are presented to demonstrate the theoretical results.