Background: Increased arterial stiffness is associated with cardiovascular morbidity and mortality among hypertensive patients. Objectives: To assess the relationship between ambulatory arterial stiffness index (AASI) and subclinical left ventricular (LV) systolic dysfunction assessed by 2-D speckle-tracking echocardiography (STE). Methods: We enrolled 70 consecutive patients with hypertension. All patients were evaluated for parameters of ambulatory blood pressure monitoring (ABPM) including AASI. From those patients, 51 underwent conventional echocardiography as well as 2-D STE to assess for subclinical LV systolic dysfunction defined by global longitudinal strain (GLS) and global circumferential strain (GCS). Results: The mean age of the patients (n = 51) was 46.3 ± 12.3 years, women represented 59%. Study population were divided into two groups according to blood pressure control as defined by ABPM; controlled (n = 23), and uncontrolled (n = 28). Baseline characteristics were comparable between both groups. There were significant differences in both daytime and night-time mean ABPM (P < 0.05). Posterior wall thickness, as well as LV relative wall thickness were significantly higher in uncontrolled patients (P < 0.05 for each). AASI was significantly, but moderately correlated to GLS. Most ABPM parameters were elevated with the higher AASI values (AASI ≥0.5). Significantly more uncontrolled hypertensive patients were encountered as well. Interestingly, sex and AASI were predictors of impaired GLS by univariate linear regression analysis; however, AASI was the only independent predictor of impaired GLS on multivariate analysis (Beta = 0.3, CI = 0.2--12, and P = 0.04). Conclusion: AASI might predict subclinical LV systolic dysfunction as assessed by global longitudinal strain. Further wide-scale studies should further explore this intriguing hypothesis.