Frontal sinus trephination (FST) has numerous applications in the treatment of acute and chronic sinus disease. This procedure involves making an incision at the medial aspect of the supraorbital rim and then drilling the sinus's anterior table. Placement of a frontal trephine allows for irrigation of the frontal recess in order to evacuate the frontal sinus in a minimally invasive manner. Orbital injury is a rare complication of FST. We present a case of previously unreported orbital compartment syndrome secondary to iatrogenic fracture of the superomedial orbital rim as a complication of frontal trephine irrigation. We also review the literature on the applications of FST and its associated complications, and we discuss orbital compartment syndrome as a complication of sinus surgery.