Non-destructive assessment of delaminations in glued laminated timber structures is required during their full life cycle. A novel air-coupled ultrasound (ACU) method has been developed, which is able to separately detect delaminations in individual bonding planes of arbitrarily high and long laminated stacks and typically 200 mm wide. The 120 kHz ACU transmitter-receiver pair is positioned at two opposite lateral faces of the sample, with a small inclination with respect to the inspected bonding planes, so that an ultrasound beam is excited at a user-defined refraction angle within the sample, interacting with defects in a limited height portion of the stack. The attenuation of the ultrasound beam transmitted across the defect (negative detection) provided better sensitivity to defects than the scattered fields (positive detection), which are masked by spurious fields. Dedicated finite-difference time-domain (FDTD) simulations provided understanding on the wave propagation and defect detectability limits, with respect to the heterogeneous anisotropic material structure introduced by the curvature of the annual rings in individual timber lamellas. A simplified analytical expression was derived to calculate refraction angles in timber in function of insonification angle and ring angle. Experimental results show that the method is able to detect >20% wide defects in both isotropic material and in glulam with straight year rings, and >50% wide and 100mm long defects in commercial glulam beams. The discrimination of defects from background variability is optimized by normalizing the images with respect to reference defect-free sample sections (normalization) or previous measurements (difference imaging), and by combining readings obtained with distinct ultrasound beam refraction angles (spatial diversity). Future work aims at the development of a tomographic defect inspection by combining the described theoretical and experimental methods.