In contemporary structural glass applications, laminated glass plays a key role, as it enhances elements beyond the dimensional limits of monolithic glass and ensures the required redundancy. As the size and expectations of glass as primary load-bearing element increase, so do laminated glass layer sizes, and along with them, the manufacturing and production possibilities. However, the design and application of layered laminated glass as primary load-bearing element such as transparent columns or masonry structures is still in its early phases compared to other structural glass elements. As a result, the Institute of Building Construction at the Technische Universität Dresden, in cooperation with Finnglass and Kuraray, investigated horizontal and vertical layered laminated glass elements under compression tests. As the interlayer of laminated glass highly affects the load-bearing behaviour and can cause early glass breakage due to induced tensile stresses, different interlayers (Standard-PVB, SentryGlas® and PVB without plasticizer) were examined in two specimen scales. This paper presents the main insights and assesses the failure modes within the experiments of layered laminated glass under uniaxial compression. Based on the examinations, constructive recommendations of layered laminated glass elements are derived.