With the planning and progress of the construction of the trans-Eurasian high-speed rail (HSR) network, it becomes an important issue for Chinese contractors to enter the European HSR market. Facing the world’s most competitive contractors and their high technology levels, Chinese contractors will need to know their advantages and disadvantages, so as to make necessary improvements. In this study, contractors for HSR are divided into two groups: construction contractors and rail equipment suppliers. In order to evaluate the competitiveness of HSR contractors, a Grey-BPNN model that combines the grey relational analysis and backpropagation neural network (BPNN) is proposed. The Grey-BPNN model is expected to analyze the overall competitiveness of Chinese contractors in the European HSR market and provide informative decision support for them. The study results show the following: (1) in the field of HSR construction, the competitiveness gap between the top-tier Chinese contractors and the most competitive international contractors is small. Chinese contractors’ competitive advantages lie in medium- and low-technology-level projects, with a strong development potential. However, they highly depend on Chinese domestic market and lack in intangible resources, like management ability and market development ability; (2) for rail equipment suppliers, China Railway Rolling Stock Corporation (CRRC) ranks among the top-tier leaders of the international market. CRRC’s greatest competitor in the European HSR market is Siemens, and CRRC is much more competitive than others in the sustainable development capability. However, CRRC needs to increase the quantity of patents and Research and Development (R&D) expenditures in transportation. As a weak transportation patent holder, CRRC has a potential risk of getting intellectual property litigations in the European HSR market.