In this paper, the existence of periodic motions of a discontinuous delayed system with a hyperbolic switching boundary is investigated. From the delay-related [Formula: see text]-function, the crossing, sliding and grazing conditions of a flow to the switching boundary are first developed. For this time-delayed discontinuous dynamical system, there are 17 classes of generic mappings in phase plane and 66 types of local mappings in a delay duration. The generic mappings are determined by subsystems in three domains and two switching boundaries. Periodic motions in such a delay discontinuous system are constructed and predicted analytically from specific mapping structures. Three examples are given for the illustration of periodic motions with or without sliding motion on the switching boundary. This paper shows how to develop switchability conditions of motions at the switching boundary in the time-delayed discontinuous systems and how to construct the specific periodic solutions for the time-delayed discontinuous systems. This study can help us understand complex dynamics in time-delayed discontinuous dynamical systems, and one can use such analysis to control the time-delayed discontinuous dynamical systems.