Background Skin cancers are the most common malignancies, and orbital and periorbital skin tumors are troublesome areas for surgeons. In this study, a series of patients diagnosed with non-melanoma skin cancer with orbital invasion was analyzed, and the surgical indications of globe-sparing surgery, reconstruction methods, complications, and outcomes were discussed. Methods This study included a series of 27 patients who underwent surgery for non-melanoma skin cancer (NMSC) with orbital invasion between June 2013 and May 2019. All surgeries were performed by a single surgeon in a single center. Results The observed success rate of the globe-sparing surgeries performed was 16/18 (89%) for patients diagnosed with BCC. Patients diagnosed with SCC had fewer benefits from their globe-sparing surgery. Half of the patients (4/8) underwent exenteration or died from distant metastasis. An early complication of globe-sparing surgery was chemosis, and all patients suffered from it for an average of 2 weeks. Late complications of globe-sparing surgery were epiphora (20/23), globe movement restriction (20/23), diplopia (17/23), and ectropion (3/23). Conclusions This study shows that orbital exenteration is a treatment with severe morbidity. Hence, every step during NMSC treatment with orbital invasion is unique to each patient and determined by in-depth and objective criteria.