Numerous studies have shown that music therapy (MT) and music listening (ML) can improve patient symptoms such as anxiety, pain, and relaxation. To investigate the effect of multiple ML sessions and the association between patient expectations and outcomes, patients were recruited from two nursing and rehabilitation centers in Roanoke, Virginia. Patients received three 30-minute ML sessions (experimental) or no intervention (control). Patient data included the Edmonton Symptom Assessment System (ESAS), vitals, and an expectations questionnaire. No difference was observed between the experimental and control groups when comparing symptoms and vitals. No correlation was observed between patient expectations and improvement in anxiety and pain (as measured by ESAS). However, patients who expected a clear improvement in anxiety demonstrated an improvement in systolic blood pressure and heart rate. Our results do not support the use of ML to improve anxiety and pain in chronically and terminally ill patients. Although no correlation was observed between patient expectations and symptom improvement, it may be helpful to utilize patient expectations when identifying those who may benefit from music interventions.