Objectives To analyze the retention forces between primary and secondary telescopic crowns milled from various materials and to compare them with the retention forces between cast telescopic crowns made of precious metal alloys. Materials and methods Primary and secondary crowns (N = 60; n = 10 per group) were fabricated using various material combinations (1: zirconia [ZIR]/polyether ether ketone [PEEK]; 2: titanium grade IV [TI]/PEEK; 3: PEEK/PEEK; 4: nonprecious alloy [NPA]/PEEK; 5:NPA/NPA), while precious alloy (PA) was used for the control group (6: PA/PA). The retention forces at 10, 1000, 5000, and 10,000 connection and disconnection cycles and the relative weights were analyzed, applying nonparametric repeated measures ANOVA and post hoc Mann–Whitney and Wilcoxon signed-rank tests (α < 0.05). Results Globally, significant differences in the retention forces among the materials (p < 0.0001), time points (p < 0.0001), and wear resistance for the various materials (p < 0.0001) were observed. No significant changes in retention forces compared to baseline were observed in groups 2, 4, 5, and 6. A significantly higher weight loss for both primary and secondary crowns was observed in groups 4 and 6. Conclusions The material combination in telescopic attachments influences retention forces and wear. Interactions between materials and time were evident, indicating that the change in retention forces differs among the materials. The combinations of milled TI/PEEK and NPA/NPA qualify for further preclinical testing in a more clinically realistic setup, determining a material-specific double-crown design. Clinical relevance The design of precious alloy telescopic crowns cannot be directly transferred to other milled material combinations due to different retention behaviors.