This paper was prepared based on in situ measurements carried out by the authors using the CPTu and DMT static penetration probes. The list of study sites includes seven specific locations in the northern parts of Croatia and one study site on the southern border of the country. The sites were selected based on the criterion of soil type, which falls into the category of soft to firm, slightly over-consolidated silty clays and silty sands. Intermediate soils are prevalent in the wider region, and most engineers deal with them in their everyday practice. For this reason, local characterization is of most importance for engineering purposes. In this investigation, results of in-situ tests are compared in order to validate the quality of the constrained modulus obtained from a CPT test to the one obtained by a DMT flat dilatometer. A comparison was made between the CPT test cone resistance and two DMT parameters—normalized modulus and horizontal stress index . Dependencies were analyzed for the main soil groups and intermediate data groups. Clay soils were divided into two subgroups based on the identification parameter , while silty soils were analyzed in three subgroups. The results for each subgroup differed significantly, and the analyses showed deviations from published values, especially for the intermediate soil groups. The usefulness of the application is demonstrated with examples at two sites, showing improvements over the most commonly used formula for the constrained modulus from the CPT test.