We describe a case of recurrent pituitary apoplexy, initially with haemorrhage into a non-functioning pituitary adenoma, and then five years later re-presented with what was found histologically to be a sellar malignant spindle and round cell neoplasm. Multiple pituitary tumours have previously been reported to coexist in the same individual, but to our knowledge this is the only case where the occurrence of two distinct de novo pituitary tumours have successively arisen in a single patient. This case is also unusual in its progressive ophthalmoplegia, including at one point a bilateral sixth nerve palsy, and in its presentation with epistaxis.