Metastatic disease presenting clinically as small intestinal tumoural masses has been described in the literature but is uncommon. It is imperative to consider the possibility of metastases before diagnosing a primary small intestinal malignancy. We hereby illustrate two such case reports of metastatic disease presenting as tumoural masses in the small intestines. First is a 63-yearold gentleman with known metastatic renal cell carcinoma (RCC) who presented with intestinal obstruction. Radiological imaging of the abdomen revealed a jejuno-jejunal intussusception, secondary to a solitary polypoid tumour. Histology of the polypoid tumour confirmed the presence of clear cell RCC. In our literature review, we note that intussusception is a common presentation in metastatic RCC to the small intestines. Hence, this clinical feature may be useful in determining a metastatic process, even in the setting of a solitary lesion. Second is a 41-year-old lady who presented with massive bleeding from the upper gastrointestinal tract. Gross examination of the distal duodeno-jejunectomy specimen reveals aggregates of reddish polypoid tumours. Histological and immunohistochemical techniques culminated in a diagnosis of metastatic choriocarcinoma. Metastatic choriocarcinoma to the small intestines is uncommon, but careful evaluation of histological features coupled with the judicious use of immunohistochemistry and a degree of suspicion can help make the correct diagnosis. In conclusion, metastatic disease masquerading as small intestinal tumoural masses is not uncommon. Judicious use of immunohistochemistry, in addition to the careful identification of pertinent clinical and histological features, can help pathologists reach the correct diagnosis.