Inflammatory fibroid polyp (IFP) of the gastrointestinal tract is a type of inflammatory pseudotumor or inflammatory myofibroblastic tumor that occurs most commonly in the stomach but also in the small and large bowel. Small-bowel IFP usually presents with intussusception. The purpose of the current study is to describe cytological features of this lesion with differential diagnoses since pathologists may be called on to render a diagnosis on fine-needle aspiration. Two cases of IFP are described with diagnostic features on imprint smears. Both were middle-aged obese women with a history of prior intra-abdominal surgical procedures who presented with signs of intestinal obstruction and were found to have a tumor causing intussusception. At intraoperative consult, scrape cytology specimens showed cellular smears with a heterogeneous population of myofibroblasts, inflammatory cells and vessels. The features together with clinical history are sufficient to suggest the diagnosis. IFP is a lesion with a characteristic morphology. The differential diagnosis includes several other lesions, hence triage of cytological specimen for culture, electron microscopy, and immunohistochemistry is important in facilitating a correct diagnosis. Although a surgical procedure may still be necessary once a diagnosis of IFP is made, treatment may be tailored for a less aggressive process.