Background: The distal biceps brachii tendon inserts proximally and posteriorly on the bicipital tuberosity of the radius and it is a forearm supinator but also contributes to flexion of the elbow. Chronic distal biceps tendon ruptures are relatively rare, often complicated by tendon and muscle retraction, and, therefore, their primary repair is difficult or impossible. The gold standard treatment of these chronic lesions is its anatomic reinsertion at the radial tuberosity after tendon reconstruction, using autograft or allograft tissue, but there is no agreement about the most appropriate surgical technique. Untreated injuries usually result in elbow joint deficits and decreased muscular strength. We report the preliminary results in a group of patients treated with a tripled autologous semitendinosus graft. Methods: In the present retrospective study, we report the results in a series of 13 patients surgically treated using tripled autologous semitendinosus graft, fixed to the residual distal biceps tendon, starting from the myotendinous junction, and using tension-slide technique (Biceps Button—Arthrex, Inc, Naples, FL 34108, USA) in association with an interference screw. Eleven males and two females, with a mean age of 46, participated in the study. Results: At mean follow-up check-in of 35 months, clinical results were assessed using the DASH score and MEPS, with a mean value of 11 points and 87 points, respectively. Tensiomyography was also performed to evaluate muscular strength. Six patients had excellent results and seven had good results. No patient had either a tendon re-rupture, or a peripheral neurological deficit, or symptomatic heterotopic ossifications. Seven patients had a mild deficit in elbow motion and six patients had a mild deficit in forearm prono-supination. Upon tensiomyography evaluation, five patients showed a mild deficit in flexion and supination strength. All patients returned to their previous daily and sporting activities. Conclusions: According to our results, in patients affected by chronic distal biceps tendon rupture, surgical treatment performed using tripled autologous semitendinosus autograft secured to the radial tuberosity using the tension-slide technique and interference screw is associated with satisfactory outcomes.