Pyoderma gangrenosum (PG) is an infrequent, aseptic neutrophilic dermatosis that can be observed in patients with systemic diseases such as inflammatory bowel disease or rheumatic disorders. Due to its rare entity, PG often constitutes a diagnostic enigma, as it simulates other skin disorders. Typically, it is displayed as painful, ulcerative lesions localized to the lower extremities. In our study, we present a case of a 67-year-old woman with recently diagnosed ulcerative colitis who presented with two painful ulcers, one on the left anterior tibia and the other one on the left subclavian area. Initially, their clinical image overlapped with skin abscess. However, taking into account patient's medical history, skin examination, sterile wound cultures and skin biopsy, the diagnosis of PG was established. The patient was completely recovered with high doses of corticosteroids, daily wound changes and surgical intervention involving loose wound edge approximation. In this study, we highlight that clinicians should always be aware of patient's medical history in such cases, in order to early diagnose PG and avoid inaccurate medical approaches which might have an impact on patients' quality of life.