Softwood is widely employed in construction and faces high demand. Australia is grappling with substantial timber scarcity, specifically related to radiata pine, which is the dominant structural timber in the construction sector. However, Australia has a significant hardwood population, which can be utilized to reduce the high demand for radiata pine. This paper aims to investigate the bond properties of both Australian softwood (radiata pine) and hardwood (shining gum). It also discusses the potential to combine softwood and hardwood in glue or cross-laminated timber by evaluating the bond properties of the radiata pine–shining gum interface. For hardwood, the effect of primer is also investigated to determine its efficacy in improving failure mode, bond strength, and stiffness. Lastly, both glulam and cross-laminated timber bonding scenarios are simulated for bond testing by examining the effect of relative fibre orientation on the bond properties of the aforementioned species individually and in combination. Instead of conventional block shear testing, which is predominantly used for same-species bond testing, push-out testing is adopted in this study. However, a comparison with block shear testing is also made in this article. The results indicated that the use of primer on hardwood reduced the inconsistencies in the bond properties and improved wood-side failure rates. It was also concluded that the effect of fibre orientation in a CLT scenario with combined hardwood and softwood failure modes can vary significantly, which leads to a higher standard deviation in the results. Nevertheless, this study outlines the challenges and opportunities for producing hardwood–softwood hybrid glue or cross-laminated timber.