(1) Introduction: Several surgical therapy options for the treatment of pathologies of the long biceps tendon (LHB) have been established. However, tenotomy, as well as established tenodesis techniques, has disadvantages, such as cosmetic deformities, functional impairments and residual shoulder pain. This study presents the first clinical and structural results of the recently introduced loop tenodesis procedure for the LHB, developed to overcome these issues. (2) Methods: 37 patients (11 women, 26 men, mean age 52 years), who underwent loop tenodesis of the LHB were examined six months after surgery. For the clinical evaluation the Constant score, as well as the LHB score, were used, complemented by elbow flexion and supination strength measurements. The integrity of the tenodesis construct was evaluated indirectly by sonographic detection of the LHB in the bicipital groove. (3) Results: Both, the overall Constant score as well as the LHB score showed significant improvements six months postoperatively, as compared to the preoperative value. Fourteen patients (38%) presented an examiner-dependent upper arm deformity, although only five patients (13%) reported subjective cosmetic deformities. Both, flexion and supination strength were preserved compared to the preoperative level. In 35 patients (95%), the tenodesis in the bicipital groove was proofed sonographically. (4) Conclusion: The loop tenodesis of the LHB provides good-to-excellent overall clinical results after a short-term follow-up of six month. The incidence of cosmetic deformities was inferior compared to conventional therapy options (tenotomy and anchor tenodesis).