Congenital dermal sinuses are a distinctive form of occult dysraphism where patients present with neurological compression, tethering, or meningitis. This is a case study of a child presenting with spina bifida with foot deformity and a chronic non-healing ulcer after excision of dermal sinus, and subsequent tethered cord due to arachnoiditis. He developed osteomyelitis and postoperatively, a non-healing ulcer, in an insensate foot. The patient was successfully managed, and complete wound healing was achieved within three months. A multidisciplinary approach to monitor, prevent and treat complications that may impact functionality, quality of life and survival of young patients with congenital dermal sinuses is needed.