Background: Osteoporosis and hypertension (HTN) are frequent and often coexisting diseases among the elderly. Recent studies suggested that both diseases may share the same etiopathology. Moreover, the treatment of hypertension can either positively or negatively affect the bone mineral density (BMD) and consequently, either improving or worsening the patients’ osteoporosis statuses, respectively. Aim: The primary aim of this study is to determine the odd ratios, pearson and spearman correlations, and the distribution rates of the HTN statuses and their corresponding anti-HTN medications, in addition to other investigated comparative variables, across two categorized cohorts; the lower risk of femoral hip osteoporotic fracture (fHOPF) cohort [Cohort I] versus the higher fHOPF cohort [Cohort II], in Jordanian cohort. Methods: The investigated studied participants were either allocated to non-HTN versus HTN cohorts (Cohort I vs Cohort II, respectively). Also, the anti-HTN medications were categorized into 6 major medication’s group; Group I-VI. Both aforementioned categorized 2 patients’ cohorts and 6 medications’ groups were analyzed via chi square test to express the comparison results as distribution rates strength of associations (odd ratios), Pearson chi-square statistic (χ 2), Goodness of Fit (G-Test of independence), and Pearson (r) and Spearman (ρ) correlations. Patients who were on thiazide or thiazide like diuretics with ACEIs or ARBs had the lowest incidence rate of higher risk of fHOPF (50%), followed by patients who were on BBs with thiazide or thiazide like diuretics (66.7%), CCBs with thiazide or thiazide like diuretics (85%), CCBs with ACEIs or ARBs (85.7%), and lastly for patients who took CCBs with or without BBS (100%) [R & ρ [-0.390±0.081 &-0.362±0.068], χ 2 & G-Test [18.685 & 18.805], p-Value [0.002 &0.002]]. Results: Overall, 206 participants who were clinically diagnosed for osteoporotic fracture risk at our rehabilitation and rheumatology clinic between Sep 2021 and Nov 2021, were studied to investigate the differences of the various investigated independent variables across the 2 dichotomized HTN related cohorts; Cohort I-II. In this study, 49.03% (101 of the eligible patients) were allocated to the non-HTN affected cohort (Cohort I) and 50.97% (101 of the overall participants) were comparatively allocated to the HTN affected cohort (Cohort II). Conclusion: The thiazide or thiazide like diuretics and ACEIs or ARBs, alone or in combination, may positively improve the femoral hip bone mineral densities and consequently mitigate the risk of osteoporotic fractures.