Increasing concerns regarding carbon emissions and climate change are prompting a shift toward the use of sustainable materials in the construction industry. Engineered timber products are gaining attention in the construction industry due to advancements in lamination techniques and adhesives as well as the renewable characteristics of wood. Bond properties play a significant role in engineered timber products. In Australia, Radiata Pine (RP, softwood) and Shining Gum (SG, hardwood) share a large proportion of local and native plantation forest resources. The present paper investigates the bond behaviours of Australian softwoods (RP–RP), hardwoods (SG–SG) and hybrid-wood (RP–SG) combinations in both parallel (PAL) and perpendicular (PER) bonding directions using one-component polyurethane adhesives. The results indicate that most of the softwood samples were subjected to wood-side (timber) failure, whereas hardwood samples failed due to delamination but exhibited higher strength and stiffness regardless of bond direction. In contrast, bond direction had a significant effect on the bond characteristics of hybrid configurations. Improved bond properties were observed when bonded in PAL directions; however, negative effects were seen when bonded in PER directions. Obtained characteristic (5th percentile) shear bond strengths for RP–RP–PAL, RP–SG–PAL and SG–SG–PAL samples were 3.88 MPa, 6.19 MPa and 8.34 MPa, whilst those for RP–RP–PER, RP–SG–PER and SG–SG–PER samples were 3.45 MPa, 2.96 MPa and 7.83 MPa, respectively.