Although pilonidal disease (PD) characterized by chronic inflammation of the skin and subcutaneous tissue most commonly seen in the intergluteal cleft, it rarely affects the umbilicus, axilla, nose, neck, interphalangeal and toe webs, and breast and intermammary cleft. Herein, we aimed to present two patients with intermammary cleft PD and to provide a literature review on this subject. The first case was a 16-year-old woman who presented to our clinic with discharge from the intermammary cleft that had first started 6 months earlier. Her physical examination revealed two sinus orifices consistent with PD. Several days after drainage and antibiotherapy, the patient was operated and all involved tissue was excised. The second case was an 18-year-old woman referred to our hospital after having undergone several drainage procedures for a pilonidal sinus detected in the intermammary cleft at an outside center. After completing preoperative tests, the patient was taken into operation and all tissues until the anterior aspect of the sternum were excised. The defects of both patients were primarily closed and no recurrent PD developed in any of them. Hidradenitis suppurativa and breast abscesses should be considered in the differential diagnoses of PD localized to the intermammary cleft or breast tissue. Drainage and antibiotherapy are the most appropriate approaches among cases presenting with abscess formation. As cosmetic issues are more of a concern with intermammary cleft PD, excision and primary closure technique may be prioritized instead of flap techniques in chronic PD.