The diagnosis and management of eyelid cancers are quite challenging. Eyelid tumours are relatively rare diverse group of diseases varied in their presentation and extent. Many benign tumours and inflammatory conditions quite frequently masquerade eyelid cancers. Eyelid cancers are not single entity but comprise a wide range of tumours with extremes of tumour biology from indolent to very aggressive histopathologic types. Compromise on aesthetics and eyelids' indispensable function of protecting the eyes during management, may lead to untoward cosmetic disfigurement and loss of vision. On the other hand, inadequate cancer clearance will also be vision threatening and life threatening due to loco regional recurrence and metastasis. To strike an optimal balance is a challenging task, to achieve 'cancer cure' with maximum preservation of function and cosmetics. In addition, the integration of other modalities of treatment, judicious selection and their sequencing require multidisciplinary discussion and joint management by different specialists. We are presenting four case scenarios, we met with in our teaching hospital with reference to literature review to emphasize that eyelid malignancies are not always simple with respect to diagnosis and management.