Visual and pressurized pipeline systems with single- and multi-undulation layouts were used to study experimentally and analyze theoretically the transient characteristics of water-air two-phase flow during water fillings in undulation pipelines based on the combination action analyses of both the communicating pipe and the gravity of the water-air two-phase flows in the descending pipe. For the single undulation pipeline, the complex two-phase flow-pattern evolutions including full pipe flow and stratified flow for low, medium, high water-filling velocity cases, respectively, lead to a great difference in transient pressure, flow-pattern and the water-filling duration. Especially for low and medium water-filling velocity cases, the hydraulic theories related to hydraulic drop and hydraulic jump were employed to investigate the entrapped air pocket evolutions in the descending pipe, and the mechanism of negative pressure at the top of the undulation pipes occurrence was analyzed. For the same multi undulating pipeline, due to the different elevations of the three undulating points along flow direction, namely three different types of pipeline layout, high-medium-low case (high elevation undulating point, medium one, and low one), low-medium-high and high-low-medium ones, their water-filling durations are significantly different, i.e. approximately 80.02 s, 227.34 s and 617.78 s. Meanwhile, there are significant differences in flow patterns in water filling, namely larger entrapped air pockets in three descending pipes for high-medium-low case, entrapped air pockets in the first two descending pipes and open channel stratified flow in the last one for low-medium-high case, some bubbles in three descending pipes for the high-low-medium case.