Ileosigmoid knotting is a rare case of intestinal obstruction that later leads to bowel necrosis. This is more common in males than females and seen more in areas with increased rates of sigmoid volvulus. The main clinical presentations are abdominal distention, abdominal pain and tenderness, vomiting, and obstipation. Definitive diagnosis is challenging due to its rarity and overlapping symptoms with other more common abdominal conditions. Delay in diagnosis and management can lead to peritonitis, necrosis of the bowel, sepsis, and eventually septic shock. Surgeons should consider ileosigmoid knotting in cases of acute abdomen, as it requires fast decision-making and intervention for a good prognosis. We present two cases of ileosigmoid knotting presenting with acute abdomen requiring emergent laparotomy with resection of necrotic bowel.