Objectives: Cavernous sinus thrombosis is most commonly a late complication of an infection of the central face or paranasal sinuses. It is generally a fulminant process with high rates of morbidity and mortality. Therefore, it needs immediate treatment. Tolosa-Hunt syndrome is a rare but not a fatal disorder caused by non-specific inflammation of the cavernous sinus or superior orbital fissure. Since both of these conditions affect the cavernous sinus and nearby structures, they have quite similar presentations. Our objective is to highlight the difficulty in differentiating these two conditions. Case Report: We report the case of a 34-year-old Malay lady who presented with history of frontal headache for two weeks followed by diplopia, unable to lift the left eye lid and projectile vomiting. On examination, she has complete ptosis with reduced vision (6/36) and restricted movement of the eye ball (3rd, 4th and 6th nerve palsies) of her left eye. Nasoendoscopy revealed pus in the left nasopharynx posterior to eustachian tube opening. CT scan revealed engorgement of the left cavernous sinus which showed enhancement post contrast injection. Mucosal thickening was seen within the left sphenoidal sinus. These features are in keeping with left cavernous sinus thrombosis, as a complication of sphenoidal sinusitis. She has been treated accordingly. On reviewing the patient, we found that she actually has three episodes of similar problem during the last five years which were resolved itself. In view of her clinical courses with the current clinical findings, this patient has been diagnosed as Tolosa-Hunt syndrome. The lesion in the CT scan was actually an inflammatory lesion. Discussion: Tolosa-Hunt Syndrome is a painful ophthalmoplegia caused by nonspecific inflammation of the cavernous sinus or superior orbital fissure(1,2,3(sic)). This disorder is uncommon. Similar presentations of impaired ocular motility, ptosis and impaired vision are known to occur in cavernous sinus thrombosis(4,5(sic)). It is also not a common condition. The history of similar attacks for a few times makes the diagnosis of Tolosa-Hunt Syndrome more likely. Relapses can be ipsilateral, contralateral or bilateral. It is a self limited disease(1,3(sic)). However, corticosteroids lessen the degree and duration of the symptoms(1,6,7(sic)). Conclusion: Cavernous sinus thrombosis and Tolosa-Hunt Syndrome are partly sharing the same clinical presentations. High suspicion of a more fatal disease sometimes is very important for the sake of the patient.