Portal vein thrombosis (PVT) is a rare but potentially severe condition that is typically associated with underlying haematological disorders, genetic mutations, or liver diseases such as cirrhosis. However, PVT resulting from acute cholecystitis is an exceedingly uncommon occurrence with few documented cases. This report describes the case of a 44-year-old man who presented with acute right upper quadrant pain and was diagnosed with acute cholecystitis complicated by left-sided PVT, which was managed with anticoagulants and laparoscopic cholecystectomy. This case underscores the complexity of managing acute cholecystitis complicated by PVT. Although anticoagulation remains the cornerstone of PVT management, concurrent surgical intervention for cholecystitis poses challenges in terms of timing and perioperative care. A multidisciplinary approach tailored to the individual patient is crucial to achieving optimal outcomes.