Sliding mode control (SMC) has been successfully applied to many practical control problems due to its attractive features such as invariance to matched uncertainties. The characteristic feature of a continuous-time SMC system is that sliding mode occurs on a prescribed manifold, where switching control is employed to maintain the state on the surface. When a sliding mode is realized, the system exhibits some superior robustness properties with respect to external matched uncertainties. However, the realization of the ideal sliding mode requires switching with an infinite frequency. Control algorithms are now commonly implemented in digital electronics due to the increasingly affordable microprocessor hardware although the essential conceptual framework of the feedback design still remains to be in the continuous-time domain. Discrete sliding mode control has been extensively studied to address some basic questions associated with the sliding mode control of discrete-time systems with relatively low switching frequencies. However, the complex dynamical behaviours due to discretization in continuous-time SMC systems have not yet been fully explored. In this thesis, the discretization behaviours of SMC systems are investigated. In particular, one of the most frequently used discretization schemes for digital controller implementation, the zero-order-holder discretization, is studied. First, single-input SMC systems are discretized, stability and boundary conditions of the digitized SMC systems are derived. Furthermore, some inherent dynamical properties such as periodic phenomenon, of the discretized SMC systems are studied. We also explored the discretization behaviours of the disturbed SMC systems. Their steady-state behaviours are discussed using a symbolic dynamics approach under the constant and periodic matched uncertainties. Next, discretized high-order SMC systems and sliding mode based observers are explored using the same analysis method. At last, the thesis investigates discretization effects on the SMC systems with multiple inputs. Some conditions are first derived for ensuring the