In multiple applications of advanced instrumentation, single-point diamond turning (SPDT) is a popular and effective process to generate novel surfaces with nanometric surface roughness and sub-micron surface irregularities, albeit at a high cost. In SPDT, precision diamond tooling contributes significantly to the process cost escalation. Hence, for SPDT, it is vital to have an optimal precision diamond tool deployment. In this article, details of comprehensive precision diamond tool selection and tool characterization are discussed. Three makes of selected ultra-precision diamond (UPD) tools and standard diamond tools (of a global make), designated as CFT, are considered for this study. In this tool bench-marking exercise, the fabrication of Cu–Be alloy predesigned precision components (PDPCs) of a critical geometry is selected. UPD and CFT tools are deployed to fabricate (under similar machining-metrology conditions) the PDPCs. These diamond tools are evaluated in terms of the quality parameters (variation in radius of curvature, form error, and surface roughness) of the workpieces. Further, to explore the progressive wear of these tools, multiple machining cycles are conducted on these workpieces, and their quality parameters are analyzed. Thus, the precision diamond tools of three makes are benchmarked against the CFT tool. Based on the final outcome of this analysis, suitable recommendations are provided to precision diamond tool manufacturers to improve their product in terms of performance and optimized costs to meet the ever-growing tooling demands of the SPDT community.