Objectives: To assess the performance of five osteoporosis clinical risk assessment tools (SCORE, ORAI, ABONE, OST and OSIRIS), in a subgroup of young postmenopausal women aged 50-64, who underwent DXA screening. Methods: The abovementioned osteoporosis risk assessment tools were calculated for 258 young postmenopausal women (aged 50-64) who had a DXA scan, in Crete/Greece. Results: Patients with a T-score≤-2.5 or a T-score≤-2.0 had a statistically significant higher value of SCORE, ORAI and ABONE and a lower value of OST, OSIRIS, and OSIRIS Adjusted Score, compared to the patients with T-score>-2.5 and T-score>-2.0, respectively. ORAI (T-score≤-2.0) and OST (T-score≤-2.5) demonstrated the highest sum of sensitivity and specificity. CHAID analysis further confirmed the relative significance of the OST tool in the osteoporosis group (T-score≤-2.5 vs. T-score>-2.5), for a cut-off of 2.8. In the other group (T-score≤-2.0 vs T-score>-2.0) the ORAI score showed a significantly important relationship for a cut-off of 8. Conclusion: OST, despite its performance limitations, correlates best with the DXA measurements of young (50-64), postmenopausal osteoporotic women, a fact which may suggest its’ potential role as a screening tool in this specific age group.