Previous case reports have highlighted various anomalous origins of the long head of the biceps tendon (LHBT) that do not originate from the superior glenoid labrum or supraglenoid tubercle. Yet, these cases were all reported as incidental findings and were not thought to cause any significant shoulder pathology. We present the magnetic resonance (MR) imaging and clinical treatment of two cases where aberrant intra-articular origins of the long head of the biceps tendon from the anterior edge of the supraspinatus tendon may have contributed to symptomatic rotator cuff pathology. Arthroscopy confirmed MR findings of partial articular-sided supraspinatus lesions in close proximity to the anomalous origins and treatment with tenodesis of the LHBT successfully relieved symptoms. Although rare occurrences with subtle and potentially misleading imaging findings, it is important to be aware of aberrant origins of the LHBT that may contribute to concomitant rotator cuff pathology.