The presented manuscript deals with the issue of evaluating the quality of transport connections in an opted territory in relation to passenger transport. The aim of this manuscript is to design a new guideline procedure to evaluate timetables, either ex post or ex ante. The very idea of objectifying the timetables' evaluation in passenger transport is that there has not yet been stipulated any relevant guideline for a comprehensive evaluation of timetables and any specific indicators for evaluating the quality of transport connections in a transport territory. First of all, the manuscript summarizes the general qualitative indicators that are consequently implemented in the particular transport territory. Determined indicators are interconnected to the existing transport territory, as well as timetable being in operation. Such an interconnection of qualitative indicators will thereafter have a synergistic effect on the evaluation of certain transport connections, or for the entire transport territory. This entails an initial point for elaborating a set of relevant criteria for the overall transport connection quality evaluation. The second part of the manuscript consists of an application of such a designed theoretical guideline to the opted transport territory, in our case, railway transport network of the South Bohemian region was chosen. The very findings of the manuscript encompass the transport connection quality evaluation in terms of adherence to the timetable from one particular tariff point to 17 other specified tariff points.