Background Jejunal tumour is a rare, uncommon tumour of the gastrointestinal (GI) tract. The symptoms and signs are vague, non-specific and frequently confused with other GI manifestations, for instance, GI bleed or obstruction. Due to its rarity, we are facing diagnostic dilemma and variation in management jejuna tumour. Methods We are reporting a case series of five patients with jejunal tumours with various presentations, for instance, obscure gastrointestinal bleed (OGIB), by far the commonest presentation follows by obstruction and abdominal pain. Presentation of OGIB and diagnosed via capsule endoscopy whereby ulcer was seen at jejunum in two patients and tumour was seen in one patient. Two patients diagnosed with jejunal tumours via contrasted CT abdomen with the presentation of abdominal pain and distension post-prandial in one patient and intestinal obstruction another patient. Push enteroscopy was used as diagnostic tool in all patients except in patient with obstruction and biopsy of lesions/ulcers taken for histology examination. Subsequently, all patients underwent laparoscopic segmental small bowel resection and intracoporeal primary anastomosis. Results The average operating time was 2.3 hours with the length of stay of 3.33 days. Patients were allow orally 24 hours postoperatively. The analgesia requirement was minimum. There were no significant complications recorded, i.e. no postoperative ileus and surgical site infection. Conclusions Traditionally, a patient with jejunal tumour often being diagnosed during laparotomy and intraoperative enteroscopy for overt GI bleed. In this modern era of medicine, we are going towards a minimally invasive approach in term of patient‘s management. Push enteroscopy should be considered in cases of overt GI bleed whereby gastroscopy and colonoscopy revealed normal findings. It’s a diagnostic tool as well as an adjunct tool to tattoo for laparoscopic jejunal resection and intracoporeal primary anastomosis. Push enteroscopy expedites the diagnosis and management of jejunal tumour. Minimally invasive surgery has a minimal interruption of the patient‘s physiology which offers quicker recovery after surgery as compared to open surgery.