Traditional methods for estimating structural deterioration are generally costly and inefficient. Recent studies have demonstrated that implementing a network of piezoelectric transducers mounted to critical regions of concrete structural members substantially increases the efficacy of the structural health monitoring (SHM) method. This study uses a recently developed electro-mechanical-admittance (EMA)-based SHM system for real-time damage diagnosis of carbon FRP (C-FRP) ropes installed as shear composite reinforcement in RC deep beams. The applied SHM technique uses the frequency response measurements of a network of piezoelectric lead zirconate titanate (PZT) patches. The proposed strengthening methods using C-FRP ropes as ETS and NSM shear reinforcement and the applied anchorage techniques significantly enhanced the strength and the overall performance of the examined beams. The retrofitted beams exhibited increased shear capacity and improved post-peak response with substantial ductility compared with the brittle failure of the non-strengthened specimens. The health condition and the potential debonding failure of the applied composite fiber material were also examined and quantified using the proposed SHM technique. Damage quantification of C-FRP ropes is achieved by comparing and assessing the values of several statistical damage indices. The experimental results demonstrated that the proposed monitoring system successfully diagnosed the region where the damage occurred by providing early warning of the forthcoming critical shear cracking of concrete and C-FRP rope debonding failures. Furthermore, the internal PZT transducers showed sound indications of the C-FRP rope’s health condition, demonstrating a direct correlation with the mechanical performance of the fibers.