Entrapped air pockets can cause failure in water distribution systems if air valves have not been appropriately designed for expelling air during filling manoeuvres performed by water utilities. One-dimensional mathematical models recently developed for studying this phenomenon do not consider the effect of blocking columns inside water pipelines. This research presents the development of a mathematical model for analysing the filling process in a pipeline with an undulating profile with various air valves, including blocking columns during starting-up water installations. The results show how different air pocket pressure peaks can be produced over transient events, which need to be analysed to ensure a successful procedure that guarantees pipeline safety during the pressure surge occurrence. In this study, an experimental set-up is analysed to observe the behaviour of two blocking columns during filling by comparing the air pocket pressure pulses.