Streptococcus pneumoniae is the most common bacterial cause of community acquired pneumonia. The current trend in Streptococcus pneumoniae infections has been the rise of multi-drug resistance in the last two decades. We present the case of a pair of 16-month old African-American fraternal twins who presented to the emergency room on the same day for symptoms consistent with pneumonia. Upon further examination, the twins showed remarkably similar symptoms, and cultures revealed penicillin-resistant Streptococcus pneumoniae in both twins. The pneumonia affected both twins in the same way, but a tomography scan did not reveal any shared anatomical abnormalities to account for this near-identical progression. In a review of literature and case reports, there are no reported cases of fraternal twins with simultaneous or non-simultaneous pneumococcal pneumonia or effusions. This case suggests that there may be possible anatomical abnormalities in the fraternal twins which were not evident in routine testing that may have led to near-identical illnesses. The pathophysiology of the simultaneous and near identical infections is not clear but may reflect subtle genetic factors in the siblings.