This study aimed to examine and compare the retention load values (RL) of different telescopic crown assemblies (Y-TZP and CoCr primary crowns with electroformed and Y-TZP secondary crowns each) with three different taper angles (0°, 1° and 2°). Thirty Y-TZP primary crowns with electroformed gold copings (Z/G group) and Y-TZP secondary crowns (Z/Z group) and 30 CoCr primary crowns with electroformed gold copings (C/G group) and Y-TZP secondary crowns (C/Z group), each with taper angles of 0°, 1° and 2°, were fabricated, respectively. With the exception of the electroformed gold copings, all specimens were Computer-Aided-Design/Computer-Aided-Manufacturing (CAD/CAM)-milled, then sintered and afterwards manually adapted. In order to stabilize the gold copings, they were fixed in a tertiary structure. The secondary crowns were constructed with a hook, which ensured self-alignment with an upper chain. Afterwards, 20 pull-off test cycles were performed in a universal testing machine under artificial saliva and after weighing the secondary crowns with a 5 kg object for 20 s. Data were analyzed by one-way and two-way Analysis of Variance (ANOVA). C/Z with 1° showed higher (p = 0.009) RL than 0° and 2° tapers. C/G at 1° also showed higher (p = 0.001) RL than at tapers of 0° and 2°. Z/G and C/G at 0° showed lower RL than Z/Z and C/Z (p < 0.001). Primary crowns had no impact on the 0° group. Z/G showed lower RL as compared to C/Z within the 1° group (p = 0.007) and Z/Z in the 2° group (p = 0.006). The primary crown material had no influence on RL. Electroformed copings showed lower RL. Further investigations for 1° as well as for the long-term performance after thermomechanical aging are necessary.