The Boston Ocular Surface Prosthesis (BOS-P) (Boston Foundation for Sight, Needham, MA) is a fluid-ventilated rigid gas-permeable scleral lens that is utilized for the treatment of irregular corneal astigmatism and severe ocular surface disease. Recent reports have highlighted the utility of the BOS-P as a therapeutic device in cases of persistent epithelial defects, corneal neovascularization, ocular graft versus host disease, and exposure keratopathy. Patients with significant cornea disease might also have glaucoma, and those who have undergone glaucoma surgery, which typically disrupts the limbus, present a challenge when fitting the BOS-P. This report describes five patients with a history of both corneal disease and glaucoma surgery who were successfully fitted with the BOS-P.