Self-assembled nano-layering resulting from interaction of the phosphate functional group of adhesive monomers with zirconia ceramic surface has been proposed. The purpose of this study was to investigate the bond strengths of two adhesive resin cements (Panavia F 2.0 and BisCem) containing phosphate monomers added with various concentrations (0.0, 1.0, 3.0, and 5.0 wt%) of triethylene glycol dimethacrylate (TEGDMA) to air-abraded zirconia ceramic. The polished/air-abraded zirconia plates (KaVo Everest® ZS-Ronde) were imaged using atomic force microscopy and the average surface roughness (Ra) values were calculated (n = 5). The surface energy parameters of the zirconia plates and the resin cements were calculated based on the extended Fowkes theory. All resin-bonded (diameter: 2.38 mm) zirconia specimens were stored in water at 37 °C for 24 h and then half of them additionally thermocycled 10,000 times before the shear bond strength (SBS) test (n = 10). Air-abrasion of zirconia surface significantly increased the γhS (hydrogen bonding component) value (p < 0.001), as well as greatly increasing the surface area (p < 0.001). For both resin cements, the γhS (dipole-dipole component) gradually increased with increasing incorporated TEGDMA concentrations, whereas the γhS gradually decreased. Overall, the addition of 3.0 wt% of TEGDMA consistently resulted in higher SBS values even after thermocycling. Under the tested condition, reducing the concentration of the adhesive monomers with phosphate functional group by adding the dimethacrylate monomer (up to 3.0 wt%) increased the bond strength between the resin cements and zirconia ceramic.