Background: The anterior bundle of the medial ulnar collateral ligament (UCL) and the forearm flexors provide primary static and dynamic stability to valgus stress of the elbow in overhead-throwing athletes. Quantitative anatomic relationships between the dynamic and static stabilizers have not been described. Purpose: To perform qualitative and quantitative anatomic evaluations of the medial elbow-UCL complex with specific attention to pertinent osseous and soft tissue landmarks. Study Design: Descriptive laboratory study. Methods: Ten nonpaired, fresh-frozen human cadaveric elbows (mean age, 54.1 years [range, 42-64 years]; all male) were utilized for this study. Quantitative analysis was performed with a 3-dimensional coordinate measuring device to quantify the location of pertinent bony landmarks and tendon and ligament footprints on the humerus, ulna, and radius. Results: The anterior bundle of the UCL attached 8.5 mm (95% CI, 6.9-10.0) distal and 7.8 mm (95% CI, 6.6-9.1) lateral to the medial epicondyle, 1.5 mm (95% CI, 0.5-2.5) distal to the sublime tubercle, and 7.3 mm (95% CI, 6.1-8.5) distal to the joint line on the ulna along the ulnar ridge. The flexor digitorum superficialis (FDS) ulnar tendinous insertion was closely related and interposed within the anterior bundle of the UCL, overlapping with 45.6% (95% CI, 38.1-53.6) of the length of the anterior bundle of the UCL. The flexor carpi ulnaris (FCU) attached 1.9 mm (95% CI, 0.8-2.9) posterior and 1.3 mm (95% CI, 0.6-3.2) proximal to the sublime tubercle and overlapped with 20.9% (95% CI, 7.2-34.5) of the area of the distal footprint of the anterior bundle of the UCL. Conclusion: The anterior bundle of the UCL had consistent attachment points relative to the medial epicondyle and sublime tubercle. The ulnar limb of the FDS and FCU tendons demonstrated consistent insertions onto the ulnar attachment of the anterior bundle of the UCL. These anatomic relationships are important to consider when evaluating distal UCL tears both operatively and nonoperatively. Excessive stripping of the sublime tubercle should be avoided during UCL reconstruction to prevent violation of these tendinous attachments. Clinical Relevance: The findings of this study enhance the understanding of valgus restraint in throwing athletes and provide insight into the difference in nonoperative outcomes between proximal and distal tears of the UCL.