Unilateral recurrent maxillary sinusitis is a common sinunasal pathology, mostly related to the ostiomeatal complex dysfunction. Although sinusitis can potentially spread to the adjacent structures, orbital cellulitis remains an exceptionally rare sequela.The authors report the unusual case of a patient who presented with recurrent maxillary sinusitis complicated by cyclic episodes of periorbital cellulitis related to ostiomeatal complex obstruction from herniated periorbital fat through an unnoticed medial orbital wall fracture. To the best of our knowledge, no other similar case has previously been reported. The possible explanation for such an unusual association is discussed.