The transportation sector is a crucial sector of the sustainability of every national economy. Previous studies highlighted the core significance of transport enterprises in European countries over the past 60 years. The long-term sustainability of enterprises is determined by their ability to gain earnings. Thus, earnings are the synonym of significance in corporate life. The purpose of this study was to capture the lever year, the trend, and the slope of the development of earnings in the transport sector before the COVID-19 pandemic. Time series of the annual earnings of the enterprises from the close countries of the V4 region were used during a 10-year period. Buishand’s test sets the change-points of the development and indicated the values of specific central lines. The year 2013 was the lever date for the earnings of 830 Slovak and 1042 Hungarian enterprises. The year 2015 was the year of momentum for 757 Polish enterprises. The development of 397 Czech enterprises was mainly influenced by the year 2014. The results of the Mann–Kendall test detected a positive trend in the series of business finance in all countries. In addition, the Sen’s slope was estimated in the transport sector for the analyzed period 2010–2019.