Two arteries connect the anterior branch of the middle meningeal artery to the lacrimal artery. One vessel, the sphenoidal artery, passes through the superior orbital fissure. The other vessel, the meningolacrimal artery, passes through the cranio-orbital foramen. An analysis of data derived from embryology, comparative anatomy, and patterns of adult variation indicates that the meningolacrimal artery is homologous with the ramus superior of the stapedial artery, an embryologically and phylogenetically primitive vessel. The sphenoidal artery probably forms late in human ontogeny and represents an evolutionary novelty. Its distribution is probably restricted to hominoids and may be exclusive to humans and orangutans (Pongo pygmaeus). The sphenoidal artery is associated with three other derived features: the sphenoparietal sinus and sulcus and a laterally expanded superior orbital fissure. The high frequency of the sphenoidal artery in Homo and Pongo probably represents a case of parallelism. The earliest paleontological evidence of an enlarged sphenoidal artery in the Hominidae occurs in Indonesian Homo erectus (Sangiran VI).