This study is a retrospective review of cases with a preoperative radiologic diagnosis of cavernous venous malformations (CVMs) over 30 years. The aim of this study was to define imaging characteristics of CVMs, which will help differentiate these lesions from other orbital masses. Fifty-seven orbital lesions consistent with CVMs were identified on CT or MRI. Fourteen of them were symptomatic and went on to have surgical resection. Nine (64%) of these lesions were confirmed to be CVMs on pathologic examination. Of the five other lesions, there were three cases of Schwannoma, one case of pleomorphic adenoma and one was a solitary fibrous tumour. The imaging studies of all cases were re-evaluated. Patchy immediate enchancement and delayed more homogenous enchancement was identified in all the CVMs. Other tumours had instantaneous diffuse enhancement and maintained this pattern throughout the post-contrast imaging. This study suggests that pattern of contrast enhancement can help differentiate CVMs from other lesions, but it is limited by its sample size and the variability of imaging techniques and equipment used.