Chronic Lymphocytic Leukemia (CLL) and Evans Syndrome represent complex hematologic disorders characterized by distinct yet interconnected pathophysiologies. This case report explores the diagnostic and therapeutic intricacies of managing concurrent CLL and Evans Syndrome in a 59-year-old male patient presenting with fatigue and petechiae. Laboratory findings revealed severe hematologic derangements indicative of advanced CLL and autoimmune hemolytic anemia (AIHA). The diagnostic journey encompassed bone marrow analysis confirming CLL and Coombs positivity suggesting Evans Syndrome, with careful exclusion of immune thrombocytopenia (ITP). Initial therapeutic interventions included steroids and intravenous immunoglobulin (IVIG) for AIHA, alongside eltrombopag for persistent thrombocytopenia. Subsequently, rituximab and venetoclax were initiated for CLL, leading to complete remission. The successful outcome underscores the importance of an integrated therapeutic approach in managing concurrent CLL and Evans Syndrome, offering insights for future clinical management of complex hematologic disorders.