To predict the sealing performance of the subsea pipeline compression connector, a semi-analytical method is proposed and verified. The leakage condition is obtained as a function of the minimum radial deflection. The semi-analytical method consists of three parts: a macroscopic analytical model for the interference process deduced based on the membrane theory, a mesoscopic two-dimensional finite element analysis of the internally turned sealing surface according to scanning electron microscope observation, and a formulation of the leakage ratio according to the Abbott–Firestone curve. The influences of the geometry parameters are analyzed. The prediction and identification of the leakage condition near the minimum preloaded deflection are investigated. Experimental tests are also carried out to verify the proposed method. The results show that, within five times the pipeline threshold of the thin wall thickness, compression connectors designed by the proposed method can create a reliable seal with a rough internally turned surface, saving 57% of the design time while reducing the machining time and costs.