Computer aided design/computer aided manufacturing (CAD/CAM) polymers for long-term dental restorations benefit from enhanced mechanical properties. However, the quantification of their bonding properties on teeth is lacking. Therefore, the aim of this study was to determine the retention strength (RS) of differently pretreated new developed polymethylmethacrylate/urethanedimethacrylate-based CAD/CAM polymer bonded on dentin. In summary, 120 human caries-free molars were prepared, and polymeric crowns were milled and pretreated (n = 20): visio.link (VL), Scotchbond Universal (SU), Monobond Plus/Heliobond (MH), Margin Bond (MB), Margin Bond mixed with acetone (1:1) (MBA) or not pretreated (CG). Half of the specimens were cemented using Variolink II and the other half with RelyX Ultimate. Specimens were stored for 24 h in distilled water and thermal cycled (5000 ×, 5 °C/55 °C). The retention load was measured and failure types were defined. RS was calculated and analyzed using both two- and one-way ANOVA with a post-hoc Scheffé-test, unpaired t-test, Kaplan–Meier with Breslow–Gehan test and chi-squared test (p < 0.05). Crowns bonded using RelyX Ultimate showed higher RS than those bonded using Variolink II. The pretreatment showed no impact on the RS. However, survival analysis within Variolink II found an impact of pretreatment. The median RS for MH was the lowest and statistically different from MB, MBA and CG. For Variolink II MH had the poorest survival as the estimated cumulative failure function of the debonded crown increased very quickly with increasing TBS. Within the RelyX Ultimate groups, no significant differences were determined. The newly developed CAD/CAM polymer showed the highest bonding properties after cementation using RelyX Ultimate.