In this paper, a new indirect digital redesign method is presented for multi-rate sampled-data control systems with cascaded and dynamic output feedback controllers. These analogue controllers are often pre-designed based on desirable frequency specifications, such as bandwidth, natural angular frequency, etc. To take advantage of the digital controller over the analogue controller, digital implementation of these analogue controllers are often desirable. As only measured input-output signals are available, an ideal state reconstructing algorithm is utilised to obtain the multi-rate discrete-time states of the original continuous-time system. Based on the Chebyshev quadrature method, the gains of the multi-rate cascaded and the output feedback digital controllers are determined from their continuous-time counterparts according to the different sampling rates employed in the different parts of the closed-loop system. As a result, the respective analogue controllers with the high-frequency and low-frequency characteristics can be implemented using the respective fast-rate sampling and slow-rate sampling digital controllers. Unlike the classical direct bilinear transform method, which is an open-loop direct digital redesign method, the proposed digital controllers take into account the state-matching of the original continuous-time closed-loop system and the digitally redesigned sampled-data closed-loop system. To further improve the state-matching performance, an improved digital redesign approach is also developed to construct the multi-rate cascaded and dynamic output feedback digital controllers. Illustrative examples are given to demonstrate the effectiveness of the developed methods.