A study was conducted to predict failure stresses, failure locations, and their paths of initiation of perforated polymethyl methacrylate (PMMA) specimens as they were loaded using pins inserted into the holes. First, a series of experiments were conducted for perforated PMMA coupons. There were six different types of coupons. The test specimens had three different widths with a circular hole of a diameter of 8 mm, which was placed at two different locations along the specimen length. All the specimens were loaded using a pin inserted into the hole with three different pins of nominal diameters of 8 mm, 6 mm, and 5 mm, respectively. To predict the failure and compare the results against the experimental data, the recently proposed universal failure criterion was used in the study using finite element analyses. The failure criteria gave acceptable results as compared to the experimental data.