Streptococcus pneumoniae endocarditis is most commonly associated with pneumonia. It is relatively uncommon disease but its severity makes it clinically relevant. We present a case and review of sinusitis complicated by both pneumococcal endocarditis and cavernous sinus thrombosis. Both endocarditis and dural sinus thrombosis are known complications of facial infections. To our knowledge, this is the first reported case of both S. pneumoniae endocarditis and dural sinus thrombosis complicating sinusitis. A case report and review of the literature is presented.