The retrosternal goiter (RSG) is a slow-growing mass often benign in nature; thyroidectomy remains the preferred standard curative treatment. This study aimed to explore the local experience of RSG with respect to the clinical presentation, classifications, management, and outcomes. A retrospective chart review was conducted to include all cases diagnosed with RSG and underwent thyroidectomy between January 1998 and December 2013. A total of 1210 patients underwent thyroidectomy; of which 30 (2.5%) patients were diagnosed to have RSG. The commonly reported symptoms were dyspnea (40%), pain and discomfort (30%), dysphagia (26.7%), and hoarseness (20%). Thirteen patients (43.3%) were completely asymptomatic. The fine-needle aspiration cytology was performed in 22 (73.3%) patients, of whom the majority was benign (77.3%). The grading classification showed that grade 1 is the most frequent (73.3%). Total bilateral thyroidectomy was the most prevailing procedure in 57% cases followed by partial thyroidectomy. All patients underwent retrosternal thyroidectomy through a cervical incision except for one case. Postoperative histopathology showed frequent benign multinodular goiter (83.3%), followed by papillary thyroid cancer (10%) and thyroiditis (6.7%). The most common complication after thyroidectomy was tracheomalacia (13.4%), transient hypocalcemia (10%), and hypoparathyroidism (6.7%). There was no intraoperative or perioperative mortality. RSG is a rare entity often presented with pressure symptoms, mostly involving anterior mediastinum and had a challenging surgical procedure. A large multicenter study is needed to include more cases in order to have a consensus on the definition and classification system for such important clinical goiter presentation.© 2020 Abdelrahman, Al-Thani, Al-Sulaiti, Tabeb, El-Menyar, licensee HBKU Press.