Offshore wind turbines play a significant role in the expansion of clean and renewable energy. However, their exposure to harsh marine environments and dynamic loading conditions poses significant challenges to their structural integrity. In particular, the grouted connection, serving as the crucial interface between the monopile and the transition piece, is susceptible to cracking and particle washout that can lead to destabilizing grout erosion over time. In this paper, we propose a microwave structural health monitoring (SHM) approach for damage detection in grouted connections based on a stepped-frequency continuous wave radar. The methodology exploits ultra-wideband (UWB) electromagnetic wave propagation in the frequency range from 100 MHz to 2 GHz, where the microwaves propagate along the concrete-type dielectric material guided by the surrounding steel cylinders. For the proof of concept, a scaled laboratory demonstrator was built that realistically models the dynamic loading experienced by a full-scale monopile. The structure was equipped with an UWB radar system using two transmitting and three receiving antennas directly coupled to the grout. For validation, a large number of other sensors, i.e., accelerometers, strain gauges, and acoustic emission sensors have also been installed and measured synchronously during the fatigue test. It is demonstrated here that the proposed SHM methodology offers a nondestructive and real-time method for assessing the structural integrity of the grouted connection directly, actively, and automatically. This has the potential to support predictive maintenance activities in the future.