"Red eyes and red rash with fever" is a common pediatric complaint; however, it is an uncommon initial presentation for staphylococcal obturator abscess with adjacent ischial osteomyelitis. The case of a 13-year-old boy who was admitted to the hospital with conjunctivitis, erythematous maculopapular lesions, and fever and had this final diagnosis is reported. The differential diagnosis included various bacterial diseases, several viral illnesses, and rickettsial disease.