The numerical simulation of four-point bending tests on glued laminated timber (GLT) beams requires an adequate description of the material behavior and of relevant failure mechanisms. The wooden lamellas, building up the GLT element, include knots, as a result of the natural tree growth process, which significantly affect the mechanical behavior. The variability of the morphology and arrangement of these knots lead to a large fluctuation, especially of strength properties, along the wooden lamellas. This leads to complex and, in general, quite brittle structural failure mechanisms of the GLT element. Such failure mechanisms can numerically be described with discrete cracks, using the framework of the extended finite element method (XFEM) for cracks without predefined positions or cohesive surfaces for cracks with predefined positions. In this work, a modeling approach to reliably estimate the bending strength and failure mechanisms of GLT beams subjected to four-point bending tests is proposed. Herein, the approach is validated by simulating replications of experimentally tested GLT beams of two beam sizes and strength classes, where each knot group is considered as a section with reduced individual stiffness and strength in exactly the same position as in the real beam. The results show that the application of quasi-brittle material failure may still result in a brittle global failure of GLT beams. The present study exemplarily shows how valuable insight into progressive failure processes can be gained by allowing the formation of continuous crack patterns. Moreover, a refined consideration of the knot geometries with such sophisticated realizations of discrete cracks may be able to simulate the actual failure mechanisms even more precisely.