Background/Objectives: The ulnar nerve’s unique anatomy makes it vulnerable to complex elbow dislocations. Depending on the nature of the injury, the clinical treatment and outcomes related to the nerve may vary. Unfortunately, the current literature provides limited and fragmented information on managing the ulnar nerve and the incidence of neuropathy in complex elbow dislocations. This study aimed to determine the occurrence of ulnar nerve pain and its relationship with transposition. Methods: A retrospective evaluation was conducted on a consecutive series of 44 patients who underwent surgery for complex elbow dislocations. The average follow-up period was 29 months. Patients were categorized based on their condition (trans-olecranon fracture–dislocation, Terrible Triad, Monteggia-like lesions, and injuries not falling into the previous categories). The study assessed whether the ulnar nerve was released from the cubital tunnel and underwent transposition. Additionally, the study examined the number of patients experiencing ulnar pain in the postoperative period and its duration over time. All patients were also evaluated using the Mayo Elbow Performance Score (MEPS), Disabilities of Arm, Shoulder, and Hand (DASH) score, and Oxford Elbow Score (OES). Results: Patients who underwent simultaneous ulnar nerve transposition surgery with complex elbow dislocation showed a higher incidence of neuropathy. In these patients, the symptoms were less severe but lasted longer. MEPS, DASH, and OES did not show statistically significant differences between the two groups; however, they were slightly better for the group without ulnar nerve transposition. Conclusions: Surgeons should refrain from routinely transposing the ulnar nerve in complex elbow dislocations. However, further studies involving larger populations are necessary.