Telescopic crowns are used to connect removable dental prostheses with the remaining dentition. Several material combinations are used for manufacturing primary and secondary crowns. The present experimental study analysed the influence of different material combinations on the long-term development of surface roughness and pull-off forces. Six different material combinations were tested. Secondary crowns were manufactured either by casting or electroforming. Each material combination was tested with n = 10 specimens. A material testing device with integrated power sensors was used for 10,000 cycles per test. Signs of wear were identified by surface roughness measurements, and visualized by a scanning electron microscope (SEM) and X-ray spectroscopy (EDX) technologies. Statistical significances were tested by using the U-Test with Bonferroni correction. The choice of materials and the manufacturing process were found to influence the long-term development of pull-off forces as well as wear-associated surface roughness. Combinations of different groups of materials for primary and secondary crowns showed favourable results. Worse results were found for the combination pure titanium and pure titanium and the combination high gold alloy and electroformed gold. Wear-associated surface roughness was higher for combinations of similar or identical groups of materials. For manufacturing telescopic crowns, combinations of different groups of materials are preferred. For secondary crown manufacturing, electroforming is superior to casting.