Good bond and water impermeability in fiber-reinforced polymer (FRP) bonded/coated systems are essential if the durability of FRP-rehabilitated concrete structures is to be ensured. In addition, water impermeability is required in some special FRP applications, such as the strengthening of underground water pipes. So far, there has been no method in the literature guaranteeing water impermeability in FRP strengthening works. This paper studies the feasibility of using a waterproof coating as the initial primer on cementitious materials before applying externally bonded FRP. In this preliminary investigation, by examining the two most important indicators (i.e., pull-off bond tests and water penetration tests), it was found that the use of an initial waterproof layer in the proposed FRP bonding system did not influence the pull-off bond strength but significantly improved the system’s water impermeability. It is, therefore, suggested that an initial waterproof layer can be included in method statements for externally bonded FRP systems to upgrade the effectiveness and durability of FRP systems.