Coupled oscillators are being studied extensively to explore different dynamical phenomena in nature and society. Time delays, namely processing delay and propagation delay play a vital role in influencing the response of a coupled oscillating system. Delay, if not negligible, is to be considered in modelling a system to replicate the system dynamics as obtained in the real world. It has a significant contribution to collective behaviour if the number of interacting components is large in the network. This chapter deals with the dynamics of a mean-field diffusive coupled Van der Pol oscillator-based system with an inherent delay in each oscillator unit. The component oscillators become unstable through inhomogeneous limit cycle (IHLC) and quasi-periodic (QP) oscillations. Analytical studies and numerical simulation have been presented to explore the coupled system response with different values of delay, diffusive coupling strength as well as number of oscillators. With the increase in delay time, coupling strength or the number of oscillators in the coupled system, the complexity of the system response is increased and the system gradually becomes unstable.