Eyelid tumours are relatively rare diverse group of diseases varied in their presentations and extent. These tumours require individually tailored distinct diagnostic and treatment considerations. Their management is usually not simple due to the functional and aesthetic importance of the eye and the periocular structures and also due to their unique metastatic behaviour. In this article, we share our experience of the cases of malignant tumours of the eyelid from a tertiary referral hospital located in a semi urban part of South India. CaSe 1A 60-year-old female presented with right upper eyelid swelling associated with pain for nine months and redness and discharge from right eye for a month. She also had eye irritation, reduced vision and inability to open eye fully. Her past history was suggestive of surgery done four years back with excision and local flap reconstruction for squamous cell carcinoma in the right upper eyelid.On examination, there was proptosis of right eye and right upper eyelid had a swelling of size 5x4 cm in the temporal aspect with ill-defined margins and overlying skin erythema. Posterior limit of the lesion could not be marked out. Conjunctival chemosis was present with corneal haziness. She also had preauricular matted lymph nodes with restricted mobility and discrete mobile level II and III cervical lymph nodes in the ipsilateral side.Contrast Enhanced Computed Tomography (CECT) showed heterogeneously enhancing extraconal mass lesion 35x30x25 mm in the right upper eyelid causing mass effect pushing the globe and lateral rectus medially with loss of fat plane. Lacrimal gland could not be visualised separately. In addition, there was a homogenously enhancing mass lesion of 45x32x22 mm involving superficial lobe of parotid with loss of fat plane between the mass and the masseter muscle, extending superficial to zygomatic arch. Multiple significant enhancing right cervical lymph nodes were present in the levels Ib, II, III, IV, Va and Vb, largest being level II node of 18x12 mm size, showing heterogenous enhancement. Clinical diagnosis of recurrent squamous cell carcinoma of right upper eyelid with multiple ipsilateral metastatic cervical lymphadenopathy including preauricular lymph nodes was arrived at. After Fine Needle Aspiration Cytology (FNAC) confirmation, case was discussed in 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 rec...