Approximately 3% of pregnant women have sickle cell disease (SCD). COVID-19, caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), became a global pandemic in March 2020, resulting in more than 3,500 deaths in Jamaica by April 2023. Sickle cell disease is an immunocompromised state; therefore, contracting COVID-19 may result in adverse maternal/neonatal outcomes. Current literature focusing on individuals of Afro-Caribbean descent is limited. Our objective was to describe the obstetric and neonatal outcomes of pregnant patients with SCD who contracted COVID-19. A retrospective case series was conducted at the University Hospital of the West Indies (Jamaica) from 2020 to 2022. We describe the maternal and neonatal outcomes of three patients with COVID-19 and SCD (including two with hemoglobin SC disease and one with hemoglobin SS disease), with complications including the demise of a mother and a newborn. Vaso-occlusive crisis was the more common presentation. Two patients required ventilatory support. Although previous reports have shown similar clinical sequelae in pregnant and nonpregnant patients with SCD and COVID-19, maternal and neonatal deaths remain possible.