Introduction: Arterial stiffness may have a significant impact on the development of cerebral small vessel disease (cSVD). Patients and methods: We obtained pulse wave velocity (24-h PWV) by means of ambulatory blood pressure monitoring (ABPM) in patients with a recent small subcortical infarct (RSSI). Patients with known cardiac or arterial embolic sources were excluded. Lacunes, microbleeds, white matter hyperintensities and enlarged perivascular spaces at baseline were assessed in a brain MRI and included in a cSVD score. A follow-up MRI was obtained 2 years later and assessed for the appearance of new lacunes or microbleeds. We constructed both unadjusted and adjusted models, and subsequently selected the optimal models based on the area under the curve (AUC) of the predicted probabilities. Results: Ninety-two patients (mean age 67.04 years, 69.6% men) were evaluated and 25 had new lacunes or microbleeds during follow-up. There was a strong correlation between 24-h PWV and age ( r = 0.942, p < 0.001). cSVD was associated with new lacunes or microbleeds when adjusted by age, 24-h PWV, NT-proBNP and hypercholesterolemia (OR 2.453, CI95% 1.381–4.358). The models exhibiting the highest discrimination, as indicated by their area under the curve (AUC) values, were as follows: 1 (AUC 0.854) – Age, cSVD score, 24-h PWV, Hypercholesterolemia; 2 (AUC 0.852) – cSVD score, 24-h PWV, Hypercholesterolemia; and 3 (AUC 0.843) – Age, cSVD score, Hypercholesterolemia. Conclusions: cSVD score is a stronger predictor for cSVD progression than age or hemodynamic parameters in patients with a RSSI.