Background: Defects resulting from gynecologic oncology resections can range from small external defects to total exenterations, requiring complex pelvic reconstruction. We aim to investigate the patient and surgical factors that influence complication rates, reoperation rates, and length of stay. We hypothesize that this patient cohort will have high complication and reoperation rates that are likely most affected by their medical and extirpative surgery factors, with less direct impact from their reconstructive surgery procedures. Methods: All cases of reconstruction following resection of a gynecological oncology tumor at the University of Wisconsin Hospital over the last 14 years were reviewed. Forty-three patients were identified who required 66 flaps for reconstruction. Results: Mean follow-up period was 19 months. Overall complication rate was 65% and reoperation rate was 33%. Plastic surgery flap-specific complication and reoperation rates were 47% and 19%, respectively, and were not significantly associated with any patient risk factors. Flap reconstruction subtype was not associated with time to complete healing, complication rate, or reoperation. Prior chemotherapy was significantly correlated with increased rate of overall complication (P = 0.0253) and reoperation (P = 0.0448), but prior radiation was not. Mean hospital stay was 11 days (SD ± 9 d). Factors found to be significantly associated with an increase in hospitalization length were increasing number of comorbidities (P = 0.021), exenteration defects (P = 0.0122), myocutaneous flap reconstruction (P = 0.0003), radiation (P = 0.0004), and chemotherapy P = 0.0035). Conclusion: This patient cohort has an overall high complication and reoperation rate; however, increasingly complex reconstruction is not associated with significant differences in complication rates or reoperation.