Small bowel diverticular disease is usually asymptomatic, but complicated small bowel diverticular disease can present as an acute abdomen, manifesting as diverticulitis, perforation, abscess, obstruction or bleeding. Due to the rarity of the disease, very few studies have been conducted on complicated small bowel diverticular disease. Therefore, there are no clear guidelines on management. General peritonitis remains the best indication for surgical management due to its correlation with high mortality and prolonged hospital stay. Traditionally, perforated small bowel diverticular disease is managed with exploratory laparotomy, primary bowel resection and anastomosis regardless of acute presentation. However, more recent studies demonstrated a trend towards conservative or less invasive surgical management. Here, we report two perforated small bowel diverticulitis cases at our institution that underwent different management and had different outcomes.