The coefficient of thermal expansion (CTE) of adhesives is considered to be a vital parameter for dental restoration due to the oral temperature fluctuation induced by hot and cold drinks in daily life. Even more challenging, the adhesives need to bond various materials with different CTE values, and mismatched thermal expansion at the interface of two materials will produce thermal stress and cause cracking, leading to bond failure. In this study, we designed and synthesized a divinyl monomer containing a dibenzocyclooctadiene (DBCOD) unit, which was incorporated into a commercial adhesive, Single Bond Universal (SBU) to prepare low CTE adhesives. The CTE value of the adhesives can be adjusted low to 6.5 ppm/K, which is much lower than that of pure SBU. Mimicking the real applying conditions, the composite resin columns were bonded to the zirconia ceramics as a dental crown with our designed adhesives, and the shear bond strength test was carried out before and after 10 000 thermal cycles between 5 and 55 °C. The shear bond strength of pure SBU retains 44.7% of its original value after 10 000 thermal cycles, while those low CTE adhesives retain 74.6% and 61.9% of shear bond strength due to less deformation and interfacial stress during thermocycling. The newly designed adhesives provide a persistent way to enhance the shear bond strength and achieve a long lifetime in tooth restoration.