Background and Objectives: Caesarean scar pregnancy (CSP) refers to placental implantation on or in the scar of a previous caesarean section and represents a potentially life-threatening condition. CSP is considered a diagnostic challenge in obstetrics, with the diagnosis relying mainly on transvaginal ultrasound (TVS) and the management depending upon case presentation and available healthcare infrastructures. Case Presentation: We present a case of 34-year-old G3P2 with a history of two-previous caesarean sections referred to the outpatient gynaecology clinic of our Department at the 7th week (7/40) of gestation with abnormal early pregnancy TVS findings, illustrating the gestational sac attached to the caesarean scar and a foetal pole with evidence of foetal cardiac activity. We discuss the outcome of an alternative combined medical and surgical approach we followed as well as an updated review of the current literature. Conclusions: The ideal management of CSP requires tertiary centers, equipment availability and experienced healthcare professionals capable of dealing with any possible complication, as well as individualized treatment based on each case presentation.