Upper GI bleeding secondary to a live foreign body (leech) is a very rare condition, causing diagnostic and therapeutic challenges. Aquatic leeches could infest the upper gastrointestinal (GI) mucosa, resulting in bleeding and/or anemia. A history of contact with a contaminated water source is necessary to establish the diagnosis. We, herein, present two cases of upper GI bleeding caused by leech infestation and a technique for extraction of the leech.