A system and method is provided for the controlled entry of a tubing string, and cable adjacent thereto, into a wellbore. A stationary housing is fit to a wellhead and has a bore in communication with the wellbore. The cable can be laterally displaced from the bore into a cable access formed into the side wall of the stationary housing for fitting a sealing assembly to the bore and engages a sealing surface therein. The sealing assembly seals tubulars passing therethrough. The cable access interrupts the sealing surface. A cable bypass sub is fit to the cable access and permits the cable to extend sealingly from above the sealing surface to the wellbore wherein the cable bypasses the sealing assembly and sealing surface. A seal reconstitutes the interrupted portion of the sealing surface at the cable access.