The purpose of this study is to assess the effect of radial head/ neck injury in association with proximal ulna fractures. Between 2006 and 2020, 107 patients presented to our academic medical center for treatment of a proximal ulna fracture and were enrolled into an IRB-approved database. Radiographs, injury details, and surgical interventions were retrospectively reviewed. Patients were classified as having an isolated proximal ulna fracture (PU), a PU fracture with an associated radial head dislocation (M-D), or a Monteggia fracture with an associated radial head fracture (M-V). Clinical and functional outcomes were assessed at follow-up to determine what differences exist between fracture patterns. Statistics were generated using Chi-squared tests for categorical variables and one-way ANOVA tests for numerical variables. While all patients ultimately healed, time to radiographic healing in the PU cohort was shorter at 3.57 ± 1.7months when compared to the M-V cohort (5.67 ± 3.8months) (p < 0.05). At follow-up, patients in the M-V cohort had poorer elbow pronation and supination when compared to the PU and M-D cohorts (p < 0.05). Patients within the PU cohort had fewer complications than those in the M-D and M-V cohorts (p < 0.05). No differences were found between the three cohorts in regard to rates of reoperation, non-union, wound infection, and nerve compression (p > 0.05). The Monteggia fracture with a concomitant radial head/neck fracture is a more disabling injury pattern when compared to an isolated proximal ulna fracture and Monteggia fracture without an associated radial head/neck fracture.