Jejunal diverticulosis (JD) is a rare clinical entity. The potential complications of this condition are discussed here through a series of cases presented to our centre. A retrospective analysis of four cases, which were diagnosed and treated, was performed. These included two cases of gastrointestinal haemorrhage, one case of perforation and one case of enterolith obstruction. All of these cases were secondary to jejunal diverticulosis and treated surgically. This was accompanied by a literature search to identify the different modalities for diagnosis and treatment of this condition. JD is rare and may lead to a diagnostic delay. Awareness of the wide spectrum of potential complications can prevent this delay.