The transportation sector requires competitive analysis to comprehend the market, identify competitors’ tactics, and make informed decisions to maintain competitive advantages and satisfy changing client demands. Competitive assessment requires objectivity and comprehensiveness, necessitating the use of mathematical and statistical methods. This research examines the competitive environment of the Russian transport sector by conducting a comprehensive analysis of the 21 largest transport enterprises in Russia. Using clustering through Ward’s method and K-means, the research categorizes the industry into four distinct competitive groups: competitive superiority, sustainable competitive position, crisis competitive position, and competitive parity. Through this segmentation, the strengths and weaknesses of each group are evaluated, providing insights into the industry’s landscape. The standout market leader identified is “Russian Railways” JSC, which is recognized for its dominant position as the primary railway company in Russia. This research contributes to the field by employing clustering algorithms to analyze the competitive dynamics of Russian transport enterprises.