Overlap syndrome is a term used to describe a condition wherein a patient has features of more than one classic inflammatory rheumatic disease like systemic lupus erythematosus, polymyositis, scleroderma and rheumatoid arthritis. Individuals with an overlap syndrome may, but need not meet, complete diagnostic criteria for one or more than one classic rheumatic disease. Mixed connective tissue disease is a specific subset of overlap syndrome wherein patients have antibodies to the U1 small nuclear ribonuclear protein (anti- U1RNP) and clinical features like hand edema, synovitis, Raynaud phenomenon, acrosclerosis and biologically or histologically proven myositis. We came across an interesting case showing clinical features of both Systemic Sclerosis and Discoid Lupus erythematosus (DLE). On complete evaluation, a final diagnosis of Diffuse Systemic Sclerosis - DLE overlap was made on the basis of histopathopathological and serological findings. Patient was started accordingly on systemic and topical medications and responded well.