A prospective 36-month cohort study was conducted involving 1,250 Iraqi patients aged 50 years and older, all with DXA-confirmed osteoporosis (T-score ≤ −2.5), to estimate the incidence of new vertebral fractures and identify independent predictors. The baseline assessment comprised a clinical history, DXA scans of the lumbar spine and hip, fasting biochemistry (including 25-hydroxyvitamin D), bone turnover markers (CTX, P1NP), and baseline lateral thoracic and lumbar radiographs. Follow-up radiographs were conducted at 36 months, with earlier assessments performed as needed based on symptoms. Two blinded musculoskeletal radiologists centrally interpreted the radiographs utilising the Genant semi-quantitative method. In a span of three years, 186 new morphometric vertebral fractures were documented in 158 patients, resulting in a cumulative incidence of 12.6% and an annualised rate of 4.2%. Seventy-six-point three percent of fractures were asymptomatic. In multivariable Cox regression analysis, the independent predictors of incident vertebral fracture included prior fragility fracture (HR 2.45, 95% CI 1.75–3.42), severe vitamin D deficiency (<12 ng/mL; HR 2.10, 95% CI 1.48–2.98), increasing age (per 5-year increment; HR 1.35, 95% CI 1.15–1.58), and lower femoral-neck T-score (per 0.5 SD decrease; HR 1.40, 95% CI 1.20–1.63). The findings indicate a significant prevalence of vertebral fractures in Iraqi patients with osteoporosis, emphasising the critical, modifiable impact of severe vitamin D deficiency in conjunction with recognised clinical risk factors.