Eye socket contracture is a well-known late complication of enucleation surgery, and the additional insult of radiotherapy at an early age causes even further fibrosis and scarring of the socket. Management of the contracted socket is challenging, and several methods have been proposed. We report a case of eye socket contracture after enucleation and radiotherapy in which multiple reconstructive procedures failed. The recurrent contracture caused difficulty in housing and retaining the eye prosthesis. We reconstructed the lower eyelid with a facial artery myomucosal flap and nasolabial flap, and the upper eyelid with a Fricke flap following reconstruction of the orbital rims (supraorbital and infraorbital rims with a calvarial bone graft, and further augmentation of the infraorbital rim with a rib bone graft). Cosmesis post-reconstruction was acceptable and the prosthesis was retained very well.