Since the introduction of Cross-laminated Timber (CLT) in Austria in the early 1990s, the adoption of this 90°-crosswise-laminated product has seen exponential growth worldwide. Compared to traditional laminated timber products (e.g., glulam), CLT provides improved dimensional stability but with reduced out-of-plane bending stiffness. To improve the bending stiffness, while maintaining relative dimensional stability, a modified orientation of the inner layers in a diagonal direction can be used. This novel product is Diagonal-Cross-laminated Timber (DCLT), a composite timber product, consisting of inner layers which are rotated at different angle-ply orientations between 0 and 90 degrees to the outer layers. To properly model the out-of-plane bending behavior of the DCLT, analytical models and finite element analysis (FEA) were used, and the results were validated by four-point bending tests performed on DCLT panels with angle-ply orientations of 10°, 20°, 40°, 70°, and a conventional CLT 90° panel. The results indicate that DCLT panels with angle-ply cross layers have a structural advantage in out-of-plane bending over traditional CLT (90°) panels. The apparent bending stiffness from DCLT 90° to DCLT ± 10° has an increase of 33%, 24%, and 35%, respectively, regarding the assessed methods of experimental, theoretical, and FEM modeling. Using these panels would allow for increased spans or load-carrying capacity for a given panel span-to-depth ratio. The development of DCLT and its introduction to the industry not only could enable the use of lower-quality timber that would not otherwise satisfy structural requirements for CLT but also could help reduce the fabrication cost of CLT due to utilizing lower amounts of fiber.