Background: Upper gastrointestinal bleeding (UGIB) is a life-threatening medical emergency characterized by bleeding from the esophagus, stomach, or duodenum. This study aims to analyze the factors associated with the occurrence of death in patients. Methods: This retrospective study was conducted in the period between 2021–2022, the hospital’s consent was obtained to view patients’ data, samples were collected from patient records in the Gastrointestinal Division of the hospital. The study included 199 patients admitted to the Gastrointestinal Division who were diagnosed with gastrointestinal bleeding at Al-Mujtahid Hospital in Damascus, the exclusion criteria included both archival errors, and cases with incomplete data that cannot be studied. Results: Out of the 199 patients, 68.8% were male and 31.2% were female. The average age of patients was 57.4 years, melena was the most prominent clinical manifestation of bleeding, with 68.2% of patients, followed by Coffee ground vomiting by 34.2%, 30.2% with a history of unexplained hypotension, and 26.1% with a history of haematemesis. The majority used the Rockall warning system with a percentage of 98.5%. The majority had concomitant heart disease 31.2%. Considering the drugs used, aspirin, corticosteroids, and clopidogrel were the top results, 39.9% of patients had a history of heart, 96.5% of patients were conscious, and endoscopy revealed active bleeding in 34.2%. 69.3% had gastric ulcers, 25.1% had esophageal varices, and the majority had a Forrest Ia rating of 32.2% and a grade III of 30.2%. 37.2% needed endoscopic intervention, 19.1% had banding, 11.6% had thermal coagulation, and 10.1% had laparotomy. Death occurred in 6.5% of patients, while 83.4% needed a surgery. Our results found a statistically significant relationship between the incidence of death and each of the advanced age, cardiac antecedents, haematemesis, Coffee ground vomiting, and esophageal varices. Conclusion: Our findings reveal the association of various factors with the incidence of death in cases of UGIB reviewed at Damascus Hospital.These results are significant but may not be generalizable, so we recommend conducting more comprehensive studies.