Cutaneous involvement of chronic lymphocytic leukemia/small lymphocytic lymphoma (CLL/SLL) is uncommon. We report on a 71-year-old male with a history of CLL of the skin in the distal extremities. The patient presented with eruptions of new lesions on the toes of his feet bilaterally, causing significant pain that limited his mobility. Cutaneous involvement of CLL is a rare presentation, and management recommendations are largely based on case reports with limited follow-up. Furthermore, assessing the duration of response, response rates, and correct sequencing of treatment is difficult due to variable use and doses of treatment. The case was treated in 2001 when newer systemic treatments were not available. Therefore, the results can also be directly related to local treatments. Based on a literature review and this case, this report provides insight into the benefits and risks of local treatment for cutaneous involvement of CLL in the extremities and how radiation can be sequenced with other options such as surgical excision and chemotherapy.