Regenerating the load-bearing tissues requires 3D scaffolds that balance the temporary mechanical function with the biological requirements. In functional tissue engineering, designing scaffolds with biomimetic mechanical properties could promote tissue ingrowth since the cells are sensitive to their local mechanical environment. This work aims to design scaffolds that mimic the mechanical response of the biological tissues under physiological loading conditions. Poly(L-lactide) (PLLA) scaffolds with varying porosities and pore sizes were made by the 3D-plotting technique. The scaffolds were tested under unconfined ramp compression to compare their stress profile under load with that of bovine cartilage. A comparison between the material parameters estimated for the scaffolds and for the bovine cartilage based on the biphasic theory enabled the definition of an optimum window for the porosity and pore size of these constructs. Moreover, the finite element prediction for the stress distribution inside the scaffolds, surrounded by the host cartilaginous tissue, demonstrated a negligible perturbation of the stress field at the site of implantation. The finite element modeling tools in combination with the developed methodology for optimal porosity/pore size determination can be used to improve the design of biomimetic scaffolds.