Fiber-reinforced polymer (FRP) has been increasingly applied to steel structures for structural strengthening or crack repair, given its high strength-to-weight ratio and high stiffness-to-weight ratio. Cracks in steel structures are the dominant hidden threats to structural safety. However, it is difficult to monitor structural cracks under FRP coverage and there is little related research. In this paper, a crack monitoring method for an FRP-strengthened steel structure deploying a microstrip antenna sensor is presented. A theoretical model of the dual-substrate antenna sensor with FRP is established and the sensitivity of crack monitoring is studied. The effects of the weak conductivity of carbon fiber reinforced polymers (CFRPs) on the performance of crack monitoring are analyzed via contrast experiments. The effects of FRP thickness on the performance of the antenna sensor are studied. The influence of structural strain on crack detection coupling is studied through strain–crack coupling experiments. The results indicate that the antenna sensor can detect cracks in steel structures covered by FRP (including CFRP). FRP thickness affects the antenna sensor’s performance significantly, while the effects of strain can be ignored. The results provide a new approach for crack monitoring of FRP-strengthened steel structures with extensive application prospects.