PURPOSE: This retrospective study reviews the quality of chest masculinization in transgender men in a single institute by elucidating factors impacting complications, secondary corrections, and trends over time. METHODS: The data comprised all transgender men receiving chest masculinization in Helsinki University Hospital between 2005 and 2018. Data were collected from patient records. Complications were classified according to the Clavien-Dindo classification. RESULTS: The study included 220 patients with a median age of 23 years. Periareolar techniques were used on 117 patients, double incision with pedicular relocation of nipple areolar complex on 60 patients, and double incision with free nipple grafts on 32 patients. Ten patients were operated with other techniques and one lacked surgical technique information. Surgically managed complications occurred in 15.4% and minor complications in 43.8%. Corrective surgery under general and local anesthesia was performed on 24.3% and 37.8%, respectively. Patients with minor complications were significantly older than reference patients. Surgical technique, comorbidities, body mass index, duration of hormonal treatment, and smoking were not associated to the development of complications or secondary corrections. The proceeding to genital surgery decreased clearly over time. CONCLUSION: We found no difference in outcomes between surgical techniques. The major complication rate was similar to previous studies. The numerous minor complications might be due to the systematic reporting. The high rate of secondary corrections could be explained with our publicly funded health care and including interventions made under local anesthesia. Patients undergoing chest masculinization should be informed regarding the risk of complications and corrective interventions.